• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    The present invention relates to novel indolylphosphine ligands, transition metal complexes having these indolylphosphine ligands, and use of transition metal complexes in catalytic and stoichiometric reactions. In particular, the prevent invention provides indolylphosphine ligands in which their steric and electronic properties are tunable with facility.
    公开号:CA2517324A1
    申请号:C2517324
    申请日:2005-09-07
    公开日:2006-03-07
    发明作者:C. Scott Browning；David H. Farrar；Edmond Lam；Nicole C. Rampersad；Julie L. Sereda；Joanne O. Yu
    申请人:C. Scott Browning；David H. Farrar；Edmond Lam；Nicole C. Rampersad；Julie L. Sereda；Joanne O. Yu；
    IPC主号:C07F9-6568
    专利说明:
    WHAT IS CLAIMED IS:1. A compound selected from one or more of a compound of formula I(a) and I(b): A A BIn P P-D-P'B In ~ In I(a) I(b) in which In is defined as an indolyl substituent of the formula II: W Nl X IIA and B each simultaneously or independently are selected from the group consisting of In as defined by formula II, R, OR, SR, NRz, C(O)R, OC(O)R, C(O)OR, OC(O)OR, and SOZR in which R is selected from the group consisting of H, C~_ zoalkyl, Cz-zoalkenyl, Cz_zoalkynyl, aryl, heteroaryl, C,_zoalkylaryl, Cz_zoalkenylaryl, Ci_ zoalkylheteroaryl, Cz_zoalkenylheteroaryl, Cz_zoalkynylaryl, Cz_zoalkynylheteroaryl, a polymer support, and a linker group to said polymer support; or A and B in formula I(a), A and In in formula I(a), A and In which are bonded to the same phosphorus atom in formula I(b) and/or B and In which are bonded to the same phosphorus in formula I(b) can be taken together to form a monocyclic or polycyclic ring system having 4 or more atoms, including the phosphorous atom to which A and B are bonded; W is selected from the group consisting of R, OR, SR, NRz, C(O)R, C(O)OR, SiR3, PRz, P(O)Rz, P(S)Rz, and SOZR in which R is selected from the group consisting of H, C1_zoalkyl, Cz_zoalkenyl, Cz_zoalkynyl, aryl, heteroaryl, C~_zoalkylaryl, Cz_ zoalkenylaryl, C,_zoalkylheteroaryl, Cz_zoalkenylheteroaryl, Cz_ZOalkynylaryl, Cz_ zoalkynylheteroaryl, a polymer support, and a linker group of said polymer support;X is selected from the group consisting of halo, NOz, SCN, R, C(O)R, OC(O)R, C(O)OR, OC(O)OR, NRz, SiR3, OR, SR and SOzR in which R is selected from the group consisting of H, Cl_zoalkyl, Cz_zoalkenyl, Cz_zoalkynyl, aryl, heteroaryl, C~_ zoalkylaryl, Cz_ZOalkenylaryl, Ci_zoalkylheteroaryl, Cz_zoalkenylheteroaryl, Cz_ zoalkynylaryl, Cz_zoalkynylheteroaryl, a polymer support, and a linker group of said polymer support; Y is selected from the group consisting of halo, R, OR, SR, NRz, NOz, C(O)R, OC(O)R, C(O)OR, OC(O)OR, CN, SCN and SOZR in which R is selected from the group consisting of H, C,_zoalkyl, Cz-zoalkenyl, CZ_zoalkynyl, aryl, heteroaryl, Cl_ zoalkylaryl, Cz_zoalkenylaryl, C1_zoalkylheteroaryl, Cz_zoalkenylheteroaryl, Cz_ zoalkynylaryl, CZ_zoalkynylheteroaryl, a polymer support, and a linker group of said polymer support; and D is selected from the group consisting of (CRz)i-6, (CRz)o-3C(O)(CRz)o-3, (CRz)o 3CR=CR(CRZ)o_3~ (CRz)o-3SiRz(CRz)o_3~ (CRz)o-3NR(CRz)o-3~ NR(CRzO-aNR~ (CRz)1_ 3PR(CRz)1_3, (CRz)o-30(CRz)o-3~ O(CRz)1_40, (CRz)o-3S(CRz)o-3~ and S(CRz)o-aS in which R is selected from the group consisting of H, C~_zoalkyl, Cz_4alkenyl, aryl, heteroaryl, C,_zoalkylaryl, Cz_zoalkenylaryl, C1_ZOalkylheteroaryl, Cz-zoalkenylheteroaryl, Cz_zoalkynylaryl, Cz_zoalkynylheteroaryl, a polymer support, and a linker group of said polymer support;wherein when A and B simultaneously or independently are In as defined by formula II, two of said In groups in formula I(a) or two of said In groups in formula I(b) which are bonded to the same phosphorus atom can be directly bonded together at the position of said In groups; or two of said In groups in formula I(a) or two of said In groups in formula I(b) which are bonded to the same phosphorus atom can be coupled together at the 3-position of said In groups to form a ring system by a connecting group Z selected from C(O), O, S, SOz, CRz, CRz-CRz, CR=CR, SiRz, and NR in which R is selected from the group consisting of H, C1_zoalkyl, Cz_zoalkenyl, Cz_ zoalkynyl, aryl, heteroaryl, C~_ZOalkylaryl, CZ_ZOalkenylaryl, C1_ZOalkylheteroaryl, Cz-2o~kenylheteroaryl, C2_zoalkynylaryl, CZ_ZOalkynylheteroaryl, a polymer support, and a linker group of said polymer support; and wherein when A and B simultaneously are In as defined by formula II, all of said In groups in formula I(a) can be coupled together at the 3-position of said In groups to form a ring system by a connecting group Z selected from N, PO, CR and SiR in which R is selected from the group consisting of H, Ci_zoalkyl, C2_2oalkenyl, Cz.zoalkynyl, aryl, heteroaryl, CI_ZOalkylaryl, Cz_zoalkenylaryl, C,.zoalkylheteroaryl, CZ_ zoalkenylheteroaryl, Cz_zoalkynylaryl, Cz_zoalkynylheteroaryl, a polymer support, and a linker group of said polymer support; and salts and solvates thereof.2. The compound according to claim 1, wherein A and B each simultaneously or independently are selected from the group consisting of In as defined by formula II, R, OR, SR, NRz, C(O)R, and OC(O)R in which R is selected from the group consisting of H, C,_,oalkyl, CZ_loalkenyl, CZ_,oalkynyl, aryl, heteroaryl, C,_ZOalkylaryl, C,_ZOall'ylheteroaryl, a polymer support, and a linker group of said polymer support;or A and B in formula I(a), A and In in formula I(a), A and In which are bonded to the same phosphorus atom in formula I(b) and/or B and In which are bonded to the same phosphorus atom in formula I(b) can be taken together to form a monocyclic or polycyclic ring system having 4 or more atoms, including the phosphorous atom to which A and B are bonded.3. The compound according to any one of claims 1 and 2, wherein A and B each simultaneously or independently are selected from the group consisting of In as defined by formula II and R in which R is aryl.4. The compound according to any one of claims 1 to 3, wherein when A and Bsimultaneously or independently are In as defined by formula II, two of said In groups in formula I(a) are directly bonded together at the 3-position of said In groups or two of said In groups in formula I(a) are coupled together at the 3-position of said In groups to form a ring system by a connecting group Z selected from C(O), O, CRz, CR2-CR2, and SiR2 in which R is selected from the group consisting of H, C1_,oalkyl, C2_loalkenyl, C2_IOalkynyl, aryl, heteroaryl, C,_ZOalkylaryl, CZ_zoalkenylaryl, C,_ zoalkylheteroaryl, CZ_ZOalkenylheteroaryl, CZ_ZOalkynylaryl, CZ_2oalkynylheteroaryl, a polymer support, and a linker group of said polymer support. S
    5. The compound according to claim 4, wherein when A and B simultaneously or independently are In as defined by formula II, two of said In groups in formula I(a) are coupled together at the 3-position of said In groups to form a ring system by a connecting group Z which is defined as CH2.
    6. The compound according to claim 1, wherein when A and B simultaneously are In as defined by formula II, all of said In groups in formula I(a) are coupled together at the 3-position of said In groups to form a ring system by a connecting group Z selected from CR and SiR in which R is selected from the group consisting of H, C1_loalkyl, CZ_roalkenyl, CZ_toalkynyl, aryl, heteroaryl, C~_zoalkylaryl, CZ_ aoalkenylaryl, Ci_ZOalkylheteroaryl, CZ_ZOalkenylheteroaryl, CZ_ZOalkynylaryl, Cz_ zo~1{Ynylheteroaryl, a polymer support, and a linker group of said polymer support.
    7. The compound according to any one of claims 1 to 3, wherein when A and Bsimultaneously or independently are In as defined by formula II, two of said In groups in formula I(b) which are bonded to the same phosphorus atom are directly bonded together at the 3-position of said In groups or two of said In groups in formula I(b) which are bonded to the same phosphorus atom are coupled together at the 3-position of said In groups to form a ring system by a connecting group Z selected from C(O), 2S O, CR2, CRZ-CR2, and SiR2 in which R is selected from the group consisting of H, CI_ ,oalkyl, CZ_,oalkenyl, Cz_,oalkynyl, aryl, heteroaryl, C1_ZOalkylaryl, CZ_ZOalkenylaryl, C,_ Zoalkylheteroaryl, CZ_ZOalkenylheteroaryl, CZ_2oalkynylaryl, CZ_2oalkynylheteroaryl, a polymer support, and a linker group of said polymer support.
    8. The compound according to any one of claims 1 to 7, wherein W is selected from the group consisting of R, C(O)R, SiR3, PR2, P(O)R2, P(S)R2, and SOZR in which R is selected from the group consisting of H, C1_~oalkyl, CZ_~oalkenyl, CZ_ ioalkynyl, aryl, heteroaryl, C~_zoalkylaryl, Cz_zoalkenylaryl, C~_zoalkylheteroaryl, Cz-zoalkenylheteroaryl, Cz_2oalkynylaryl, Cz-zoalkynylheteroaryl, a polymer support, and a linker group of said polymer support.5 9. The compound according to any one of claims 1 to 7, wherein X is selected from the group consisting of halo, R, C(O)R, OC(O)R, C(O)OR, NRz, OR and SRand in which R is selected from the group consisting of H, C,_ioalkyl, Cz_loalkenyl, Cz_ ~oalkynyl, aryl, heteroaryl, C1_zoalkylaryl, Cz_zoalkenylaryl, C1_ZOallcylheteroaryl, Cz_ zoalkenylheteroaryl, C2_zoalkynylaryl, CZ_zoalkynylheteroaryl, a polymer support, and a 10 linker group of said polymer support.10. The compound according to any one of claims 1 to 7, wherein Y is selected from the group consisting of R, OR, NOz, C(O)R, OC(O)R, C(O)OR, and CN in which R is selected from the group consisting of H, C,_,oalkyl, Cz_,oalkenyl, Cz_ 15 ~oalkynyl, aryl, heteroaryl, Ci_zoalkylaryl, Cz_zoalkenylaryl, C,_zoalkylheteroaryl, Cz_ zoalkenylheteroaryl, Cz_zoalkynylaryl, Cz_zoalkynylheteroaryl, a polymer support, and a linker group of said polymer support.11. The compound according to claim 1, wherein D is selected from the group 20 consisting of (CR2)1~4, (CRz)o-zC(O)(CRZ)o_2, (CRZ)o_~CR=CR(CRz)o_,, (CRz)o-iSiRz(CRz)o-n (CRz)o-zNR(CRz)o_z, NR(CRzO-zNR> (CRzO-3pR(CRz)i.3~ (CRz)o_ z0(CRz)o-z, O(CRz)I_z0, (CRz)o-zS(CRz)o_z, and S(CRz)o_zS in which R is selected from the group consisting of H, C,_~oallcyl, CzAalkenyl, aryl, heteroaryl, C,_zoalkylaryl, Cz-zoalkenylaryl, C~_2oalkylheteroaryl, C2_2oalkenylheteroaryl, CZ_zoalkynylaryl, C2_ 25 zoalkynylheteroaryl, a polymer support, and a linker group of said polymer support.12. The compound according to claim l, selected from the group consisting of: Y X ~ W N NEW X ~ X ~ W W W Y I N X Y I(a)(i) I(a)(ii) N X W W N Y Y I(a)(iii) I(a)(iv) W W ~ v A~ /B N N P ~ ~ 'Y A Z ~ N,W y. N P~y~~ I B Y X Y I(a)(v) I(a)(vi) and I(b)(i) x x Yin which A, B, W, X, Y, Z and D are as defined in claim 1.13. The compound according to any one of claims 1 to 12, selected from the group consisting of:biphenyl-2-(3-methylindolyl)phosphine (DPIP); Phenyl-di-2-(3-methylindolyl)phosphine (PDIP); Di(1H-3-indolyl)methane-(2,12)-phenylphosphine (DIMPP);biphenyl-2-( 1,3-methylindolyl)phosphine;biphenyl-2-( 1-benzyl-3-methylindolyl)phosphine;biphenyl-2-[1-(2,3,4,5,6-pentafluorobenzyl)-3-methylindolyl]phosphine;biphenyl-2-(1-(R)-(-)-myrtenyl-3-methylindolyl)phosphine;biphenyl-2-( 1-(S~-(-)-perillyl-3-methylindolyl)phosphine; Phenyl-di-2-( 1,3-dimethylindolyl)phosphine; Phenyl-di-2-( 1-benzyl-3-methylindolyl)phosphine; Phenyl-di-2-[ 1-(2,3,4,5,6-pentafluorobenzyl)-3-methylindolyl]phosphine; Phenyl-di-2-(1-(R)-(-)-myrtenyl-3-methylindolyl)phosphine; Phenyl-di-2-( 1-(~S~-(-)-perillyl-3-methylindolyl)phosphine; Di(1-methyl-3-indolyl)methane-(2,12)-phenylphosphine; Di( 1-benzyl-3-indolyl)methane-(2,12)-phenylphosphine; Di[1-(2,3,4,5,6-pentafluorbenzyl)-3-indolyl]methane-(2,12)-phenylphosphine; W ~ ~ W P iP D Di(1-(R)-(-)-myrtenyl-3-indolyl)methane-(2,12)-phenylphosphine; Di( I -(S~-(-)-perillyl-3-indolyl)methane-(2, I 2)-phenylphosphine; Tris-2-(3-methylindolyl)phosphine (TMIP); and 1,2-[Di-2-(3-methylindole)]phosphinoethane (DIPS).14. A complex comprising a compound as defined in any one of claims 1 to 13 and a transition metal.15. The complex according to claim 14, wherein the transition metal is selected from Groups 4, 6, 8, 9 and 10 of the Periodic Table.16. The complex according to claim 15, wherein the transition metal is selected from the group consisting of titanium, zirconium, iridium, rhodium, ruthenium, palladium, platinum, cobalt and nickel.17. A use of a complex according to claim 14 as a catalyst in a reaction selected from the group consisting of hydrogenation, transfer hydrogenation, isomerization, metathesis, carbonylation, hydroformylation, Heck reaction, cross-coupling reaction, hydroamination, allylic alkylation, conjugate-addition, Diels-Alder reaction, hydrosilylation, hydrocyanation, hydroboration, copolymerization and terpolymerisation.18. The use according to claim 17, wherein the reaction is Heck reaction.19. A use of a complex according to claim 14 for stoichiometric reactions.
    权利要求:
    Claims (19)
    [1] 1. A compound selected from one or more of a compound of formula I(a) and I(b): in which In is defined as an indolyl substituent of the formula II: A and B each simultaneously or independently are selected from the group consisting of In as defined by formula II, R, OR, SR, NR2, C(O)R, OC(O)R, C(O)OR, OC(O)OR, and SO2R in which R is selected from the group consisting of H, C1-20alkyl, C2-20alkenyl, C2-20alkynyl, aryl, heteroaryl, C1-20alkylaryl, C2-20alkenylaryl, C1-20alkylheteroaryl, C2-20alkenylheteroaryl, C2-20alkynylaryl, C2-20alkynylheteroaryl, a polymer support, and a linker group to said polymer support; or A and B in formula I(a), A and In in formula I(a), A and In which are bonded to the same phosphorus atom in formula I(b) and/or B and In which are bonded to the same phosphorus in formula I(b) can be taken together to form a monocyclic or polycyclic ring system having 4 or more atoms, including the phosphorous atom to which A and B are bonded; W is selected from the group consisting of R, OR, SR, NR2, C(O)R, C(O)OR, SiR3, PR2, P(O)R2, P(S)R2, and SO2R in which R is selected from the group consisting of H, C1-20alkyl, C2-20alkenyl, C2-20alkynyl, aryl, heteroaryl, C1-20alkylaryl, 20alkenylaryl, C1-20alkylheteroaryl, C2-20alkenylheteroaryl, C2-20alkynylaryl, 20alkynylheteroaryl, a polymer support, and a linker group of said polymer support; X is selected from the group consisting of halo, NO2, SCN, R, C(O)R, OC(O)R, C(O)OR, OC(O)OR, NR2, SiR3, OR, SR and SO2R in which R is selected from the group consisting of H, C1-20alkyl, C2-20alkenyl, C2-20alkynyl, aryl, heteroaryl, C1-20alkylaryl, C2-20alkenylaryl, C1-20alkylheteroaryl, C2-20alkenylheteroaryl, 20alkynylaryl, C2-20alkynylheteroaryl, a polymer support, and a linker group of said polymer support; Y is selected from the group consisting of halo, R, OR, SR, NR2, NO2, C(O)R, OC(O)R, C(O)OR, OC(O)OR, CN, SCN and SO2R in which R is selected from the group consisting of H, C1-20alkyl, C2-20alkenyl, C2-20alkynyl, aryl, heteroaryl, C1-20alkylaryl, C2-20alkenylaryl, C1-20alkylheteroaryl, C2-20alkenylheteroaryl, 20alkynylaryl, C2-20alkynylheteroaryl, a polymer support, and a linker group of said polymer support; and D is selected from the group consisting of (CR2)1-6, (CR2)0-3C(O)(CR2)0-3, (CR2)0-3CR=CR(CR2)0-3, (CR2)0-3SiR2(CR2)0-3, (CR2)0-3NR(CR2)0-3, NR(CR2)1-4NR, (CR2)1-3PR(CR2)1-3, (CR2)0-3O(CR2)0-3, O(CR2)1-4O, (CR2)0-3S(CR2)0-3, and S(CR2)0-4S in which R is selected from the group consisting of H, C1-20alkyl, C2-4alkenyl, aryl, heteroaryl, C1-20alkylaryl, C2-20alkenylaryl, C1-20alkylheteroaryl, C2-20alkenylheteroaryl, C2-20alkynylaryl, C2-20alkynylheteroaryl, a polymer support, and a linker group of said polymer support;wherein when A and B simultaneously or independently are In as defined by formula II, two of said In groups in formula I(a) or two of said In groups in formula I(b) which are bonded to the same phosphorus atom can be directly bonded together at the position of said In groups; or two of said In groups in formula I(a) or two of said In groups in formula I(b) which are bonded to the same phosphorus atom can be coupled together at the 3-position of said In groups to form a ring system by a connecting group 2 selected from C(O), O, S, SO2, CR2, CR2-CR2, CR=CR, SiR2, and NR in which R is selected from the group consisting of H, C1-20alkyl, C2-20alkenyl, 20alkynyl, aryl, heteroaryl, C1-20alkylaryl, C1-20alkenylaryl, C1-20alkylheteroaryl, C2-20alkenylheteroaryl, C2-20alkynylaryl, C2-20alkynylheteroaryl, a polymer support, and a linker group of said polymer support; and wherein when A and B simultaneously are In as defined by formula II, all of said In groups in formula I(a) can be coupled together at the 3-position of said In groups to form a ring system by a connecting group Z selected from N, PO, CR and SiR in which R is selected from the group consisting of H, C1-20alkyl, C2-20alkenyl, 20alkynyl, aryl, heteroaryl, C1-20alkylaryl, C1-20alkenylaryl, C1-20alkylheteroaryl, C2-20alkenylheteroaryl, C2-20alkynylaryl, C2-20alkynylheteroaryl, a polymer support, and a linker group of said polymer support; and salts and solvates thereof.
    [2] 2. The compound according to claim 1, wherein A and B each simultaneously or independently are selected from the group consisting of In as defined by formula II, R, OR, SR, NR2, C(O)R, and OC(O)R in which R is selected from the group consisting of H, C1-10alkyl, C2-10alkenyl, C2-10alkynyl, aryl, heteroaryl, C1-20alkylaryl, C1-20alkylheteroaryl, a polymer support, and a linker group of said polymer support;or A and B in formula I(a), A and In in formula I(a), A and In which are bonded to the same phosphorus atom in formula I(b) and/or B and In which are bonded to the same phosphorus atom in formula I(b) can be taken together to form a monocyclic or polycyclic ring system having 4 or more atoms, including the phosphorous atom to which A and B are bonded.
    [3] 3. The compound according to any one of claims 1 and 2, wherein A and B each simultaneously or independently are selected from the group consisting of In as defined by formula II and R in which R is aryl.
    [4] 4. The compound according to any one of claims 1 to 3, wherein when A and Bsimultaneously or independently are In as defined by formula II, two of said In groups in formula I(a) are directly bonded together at the 3-position of said In groups or two of said In groups in formula I(a) are coupled together at the 3-position of said In groups to form a ring system by a connecting group Z selected from C(O), O, CR2, CR2-CR2, and SiR2 in which R is selected from the group consisting of H, C1-10alkyl, C2-10alkenyl, C2-10alkynyl, aryl, heteroaryl, C1-20alkylaryl, C2-20alkenylaryl, C1-20alkylheteroaryl, C2-20alkenylheteroaryl, C2-20alkynylaryl, C2-20alkynylheteroaryl, a polymer support, and a linker group of said polymer support.
    [5] 5. The compound according to claim 4, wherein when A and B simultaneously or independently are In as defined by formula II, two of said In groups in formula I(a) are coupled together at the 3-position of said In groups to form a ring system by a connecting group Z which is defined as CH2.
    [6] 6. The compound according to claim 1, wherein when A and B simultaneously are In as defined by formula II, all of said In groups in formula I(a) are coupled together at the 3-position of said In groups to form a ring system by a connecting group Z selected from CR and SiR in which R is selected from the group consisting of H, C1-10alkyl, C2-10alkenyl, C2-20alkynyl, aryl, heteroaryl, C2-20alkylaryl, 20alkenylaryl, C1-20alkylheteroaryl, C2-20alkenylheteroaryl, C2-20alkynylaryl, 20alkylheteroaryl, a polymer support, and a linker group of said polymer support.
    [7] 7. The compound according to any one of claims 1 to 3, wherein when A and Bsimultaneously or independently are In as defined by formula II, two of said In groups in formula I(b) which are bonded to the same phosphorus atom are directly bonded together at the 3-position of said In groups or two of said In groups in formula I(b) which are bonded to the same phosphorus atom are coupled together at the 3-position of said In groups to form a ring system by a connecting group Z selected from C(O), O, CR2, CR2-CR2, and SiR2 in which R is selected from the group consisting of H, C1-10alkyl, C2-10alkenyl, C2-10alkynyl, aryl, heteroaryl, C1-20alkylaryl, C2-20alkenylaryl, C1-20alkylheteroaryl, C2-10alkenylheteroaryl, C2-20alkynylaryl, C2-20alkynylheteroaryl, a polymer support, and a linker group of said polymer support.
    [8] 8. The compound according to any one of claims 1 to 7, wherein W is selected from the group consisting of R, C(O)R, SiR3, PR2, P(O)R2, P(S)R2, and SO2R in which R is selected from the group consisting of H, C1-10alkyl, C2-10alkenyl, 10alkynyl, aryl, heteroaryl, C1-20alkylaryl, C1-20alkenylaryl, C1-20alkylheteroaryl, C2-20alkenylheteroaryl, C2-20alkynylaryl, C2-20alkynylheteroaryl, a polymer support, and a linker group of said polymer support.
    [9] 9. The compound according to any one of claims 1 to 7, wherein X is selected from the group consisting of halo, R, C(O)R, OC(O)R, C(O)OR, NR2, OR and SRand in which R is selected from the group consisting of H, C1-10alkyl, C2-10alkenyl, C2-10alkynyl, aryl, heteroaryl, C1-20alkylaryl, C2-20alkenylaryl, C1-20alkylheteroaryl, C2-20alkenylheteroaryl, C2-20alkynylaryl, C2-20alkynylheteroaryl, a polymer support, and a linker group of said polymer support.
    [10] 10. The compound according to any one of claims 1 to 7, wherein Y is selected from the group consisting of R, OR, NO2, C(O)R, OC(O)R, C(O)OR, and CN in which R is selected from the group consisting of H, C1-10alkyl, C1-20alkenyl, 10alkynyl, aryl, heteroaryl, C1-20alkylaryl, C2-20alkenylaryl, C1-20alkylheteroaryl, C2-20alkenylheteroaryl, C2-20alkynylaryl, C2-20alkynylheteroaryl, a polymer support, and a linker group of said polymer support.
    [11] 11. The compound according to claim 1, wherein D is selected from the group consisting of (CR2)1-4, (CR2)0-2C(O)(CR2)0-2, (CR2)0-1CR=CR(CR2)0-1, (CR2)0-1SiR2(CR2)0-1 (CR2)0-2NR(CR2)0-2, NR(CR2)1-2NR, (CR2)1-3PR(CR2)1-3, (CR2)0-2O(CR2)0-2, O(CR2)1-2O, (CR2)0-2S(CR2)0-2, and S(CR2)0-2S in which R is selected from the group consisting of H, C1-10alkyl, C2-4alkenyl, aryl, heteroaryl, C1-20alkylaryl, C2-20alkenylaryl, C1-20alkylheteroaryl, C2-20alkenylheteroaryl, C2-20alkynylaryl, C2-20alkynylheteroaryl, a polymer support, and a linker group of said polymer support.
    [12] 12. The compound according to claim 1, selected from the group consisting of: in which A, B, W, X, Y, Z and D are as defined in claim 1.
    [13] 13. The compound according to any one of claims 1 to 12, selected from the group consisting of:Diphenyl-2-(3-methylindolyl)phosphine (DPIP); Phenyl-di-2-(3-methylindolyl)phosphine (PDIP); Di(1H-3-indolyl)methane-(2,12)-phenylphosphine (DIMPP);Diphenyl-2-(1,3-methylindolyl)phosphine; Diphenyl-2-(1-benzyl-3-methylindolyl)phosphine; Diphenyl-2-[1-(2,3,4,5,6-pentafluorobenzyl)-3-methylindolyl]phosphine; Diphenyl-2-(1-(R)-(-)-myrtenyl-3-methylindolyl)phosphine; Diphenyl-2-(1-(S)-(-)-perillyl-3-methylindolyl)phosphine; Phenyl-di-2-(1,3-dimethylindolyl)phosphine; Phenyl-di-2-(1-benzyl-3-methylindolyl)phosphine; Phenyl-di-2-[1-(2,3,4,5,6-pentafluorobenzyl)-3-methylindolyl]phosphine; Phenyl-di-2-(1-(R)-(-)-myrtenyl-3-methylindolyl)phosphine; Phenyl-di-2-(1-(S)-(-)-perillyl-3-methylindolyl)phosphine; Di(1-methyl-3-indolyl)methane-(2,12)-phenylphosphine; Di(1-benzyl-3-indolyl)methane-(2,12)-phenylphosphine; Di[1-(2,3,4,5,6-pentafluorbenzyl)-3-indolyl]methane-(2,12)-phenylphosphine; Di(1-(R)-(-)-myrtenyl-3-indolyl)methane-(2,12)-phenylphosphine;Di(1-(S)-(-)-perillyl-3-indolyl)methane-(2,12)-phenylphosphine; Tris-2-(3-methylindolyl)phosphine (TMIP); and 1,2-[Di-2-(3-methylindole)]phosphinoethane (DIPE).
    [14] 14. A complex comprising a compound as defined in any one of claims 1 to 13 and a transition metal.
    [15] 15. The complex according to claim 14, wherein the transition metal is selected from Groups 4, 6, 8, 9 and 10 of the Periodic Table.
    [16] 16. The complex according to claim 15, wherein the transition metal is selected from the group consisting of titanium, zirconium, iridium, rhodium, ruthenium, palladium, platinum, cobalt and nickel.
    [17] 17. A use of a complex according to claim 14 as a catalyst in a reaction selected from the group consisting of hydrogenation, transfer hydrogenation, isomerization, metathesis, carbonylation, hydroformylation, Heck reaction, cross-coupling reaction, hydroamination, allylic alkylation, conjugate-addition, Diels-Alder reaction, hydrosilylation, hydrocyanation, hydroboration, copolymerization and terpolymerisation.
    [18] 18. The use according to claim 17, wherein the reaction is Heck reaction.
    [19] 19. A use of a complex according to claim 14 for stoichiometric reactions.
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    2008-09-08| FZDE| Dead|
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    US60724904P| true| 2004-09-07|2004-09-07||
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