Method for the cyclotrimerization of alkynes in aqueous solutions
AssigneeNeXstar Pharmaceuticals, Inc.
InventorsBruce Eaton, Matthew S. Sigman
Life of this patent
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Abstract
This invention discloses an improved method for the 2+2+2! cyclotrimerization reaction in aqueous solutions using a water soluble transition metal catalyst.
Claims19
A water soluble transition metal catalyst having the general formula R.sub.x --C--M--L, wherein:
- C denotes an indenyl group;
- R is an electron withdrawing group selected from the group consisting of a nitrile, ester, ketone, amide, chloro, or fluoro;
- X=0, 1 or 2;
- M is a transition metal selected from the group consisting of Rh or Ir;
- and
- L is a ligand selected from the group consisting of two separate 2 electron .pi.-ligands or one 4 electron .pi.-ligand of a transition metal.
A water soluble transition metal catalyst having the general formula R.sub.x --C--M--L, wherein:
- C denotes a cyclopentadienyl or indenyl group;
- R is an electron withdrawing group selected from the group consisting of a nitrile, ester, ketone, amide, chloro, or fluoro;
- wherein R also contains a polar functional group selected from the group consisting of an amine, amide, sulfoxide, sulfonate, hydroxyl, guanidinium, polyamine, putracene, or spermadine;
- X=0, 1 or2;
- M is a transition metal selected from the group consisting of Co, Rh or Ir;
- and
- L is a ligand selected from the group consisting of two separate 2 electron .pi.-ligands or one 4 electron .pi.-ligand of a transition metal.
A water soluble transition metal catalyst having the general formula:
- ##STR16## wherein R is an electron withdrawing group selected from the group consisting of a nitrile, ester, ketone, amide, chloro or fluoro;
- and M is a transition metal selected from the group consisting of Rh or Ir.
A water soluble transition metal catalyst having the general formula:
- ##STR17## wherein R is an electron withdrawing group selected from the group consisting of a nitrile, ester, ketone, amide, chloro or fluoro;
- and M is a transition metal selected from the group consisting of Co, Rh or Ir.;
- and R.sub.3 is a polar functional group selected from the group consisting of an amine, sulfonate, hydroxyl, guanidinium, polyamine, putracene, or spermadine.
A water soluble transition metal catalyst having the general formula:
- ##STR18## wherein R is an electron withdrawing group selected from the group consisting of a nitrile, ester, ketone, amide, chloro or fluoro;
- and M is a transition metal selected from the group consisting of Co, Rh or Ir.;
- and R.sub.3 is a polar functional group selected from the group consisting of an amine, sulfonate, hydroxyl, guanidinium, polyamine, putracene, or spermadine;
- and n=1-8.
A water soluble transition metal catalyst having the formula:
- ##STR19##
A water soluble transition metal catalyst having the formula:
- ##STR20##
A water soluble transition metal catalyst having the general formula R.sub.x --Cp--Co--L, wherein:
- R is an electron withdrawing group selected from the group consisting of a nitrile, amide, or fluoro;
- X=1 or 2;
- and
- L is a ligand selected from the group consisting of two separate 2 electron .pi.-ligands or one 4 electron .pi.-ligand of a transition metal.
A water soluble transition metal catalyst having the general formula:
- ##STR21## wherein R is an electron withdrawing group selected from the group consisting of a nitrile, amide or fluoro.
A water soluble transition metal catalyst having the general formula R.sub.x --C--Co--M--L, wherein:
- C denotes an indenyl group;
- R is an electron withdrawing group selected from the group consisting of a nitrile, ester, ketone, amide, chloro, or fluoro;
- X=1 or 2;
- and
- L is a ligand selected from the group consisting of two separate 2 electron .pi.-ligands or one 4 electron .pi.-ligand of a transition metal.
A water soluble transition metal catalyst having the general formula R.sub.x --C--Co--L.sub.y, wherein:
- C denotes an indenyl group;
- R is an electron withdrawing group selected from the group consisting of a nitrile, ester, ketone, amide, chloro, or fluoro;
- X=0, 1 or 2;
- L is a ligand selected from the group consisting of ethenes, propenes, butenes, pentenes, cyclopentenes, hexenes, cyclohexenes, cyclobutadiene or cyclohexadiene;
- and
- y=1 or 2.
A water soluble transition metal catalyst having the general formula R.sub.x --C--Co--L, wherein:
- C denotes an indenyl group;
- R is an electron withdrawing group selected from the group consisting of a nitrile, ester, ketone, amide, chloro, or fluoro;
- X=1 or 2;
- and
- L is cyclooctadiene.
A water soluble transition metal catalyst having the general formula R.sub.x --Cp--Rh--L, wherein:
- R is an electron withdrawing group selected from the group consisting of a nitrile, ester, amide, or fluoro;
- X=0, 1 or 2;
- and
- L is a ligand selected from the group consisting of two separate 2 electron .pi.-ligands or one 4 electron .pi.-ligand of a transition metal.
A water soluble transition metal catalyst having the general formula R.sub.x --Cp--Rh--L.sub.2, wherein:
- R is an electron withdrawing group selected from the group consisting of a nitrile, ester, ketone, amide, chloro or fluoro;
- X=0, 1 or 2;
- and
- L is a ligand selected from the group consisting of propenes, butenes, pentenes, cyclopentenes, hexenes, cyclohexenes, cyclobutadiene, cyclohexadiene or cyclooctadiene;
- and
- y=1 or 2.
A water soluble transition metal catalyst having the general formula R.sub.x --Cp--Ir--L, wherein:
- R is an electron withdrawing group selected from the group consisting of a nitrile, ester, amide, chloro or fluoro;
- X=0, 1 or 2;
- and
- L is a ligand selected from the group consisting of two separate 2 electron .pi.-ligands or one 4 electron .pi.-ligand of a transition metal.
A water soluble transition metal catalyst having the general formula R.sub.x --Cp--Ir--L.sub.2, wherein:
- R is an electron withdrawing group selected from the group consisting of a nitrile, ester, ketone, amide, chloro or fluoro;
- X=0, 1 or 2;
- and
- L is a ligand selected from the group consisting of propenes, butenes, pentenes, cyclopentenes, hexenes, cyclohexenes, cyclobutadiene, cyclohexadiene or cyclooctadiene;
- and
- y=1 or 2.
Dependencies are inferred from the claim text.