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US 8,481,746 B2Granted
Diarylphosphine-containing compounds, processes of preparing same and uses thereof as tridentate ligands
AssigneeTechnion Research & Development Foundation Limited
InventorsMark Gandelman, Elaine Melissa Schuster
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Abstract
A novel process of preparing tridentate ligands containing a diarylphosphine electron donating group are disclosed. Use of this process for preparing a combinatorial library of such tridentate ligands and of organometallic complexes containing same is also disclosed. Further disclosed are novel diarylphosphine-containing compounds that can serve as tridentate ligands (e.g., pincer ligands), combinatorial libraries of such tridentate ligands, organometallic complexes containing these ligands (e.g., pincer complexes), and combinatorial libraries of such complexes. Methods utilizing these libraries for screening for candidate organometallic catalysts are also disclosed.
Claims25
A compound of the general Formula I:
- wherein:
- n is an integer from 1 to 4;
- R1-R4 are each independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl, heteroaryl, heteroalicyclic, alkoxy, thioalkoxy, hydroxy, thiol, amine, nitro and cyano;
- R5 is a leaving group capable of being dissociated so as to form a carbanion;
- D1 is an electron donating group of the general Formula IIa:
- Z1Z2Xa Formula IIa;
- and
- D2 is an electron donating group of the general Formula IIb:
- Z3Z4Xb Formula IIb;
- whereas:
- Xa and Xb are each independently an electron donating atom;
- and
- Z1, Z2, Z3 and Z4 are each independently absent or a substituent selected from the group consisting of substituted or non-substituted aryl, substituted or non-substituted alkyl, substituted or non-substituted alkoxy and substituted or non-substituted aryloxy, or, alternatively, at least two of Z1, Z2, R1 and R2 and/or at least two of Z3, Z4, R3 and R4 from together a five- or six-membered heteroalicyclic or heteroaromatic ring,
- wherein each of said electron donating atoms Xa and Xb is independently selected from the group consisting of phosphorous, sulfur, nitrogen and carbon, said carbon being a carbene that forms a part of a N-heteroalicyclic or a N-heteroaryl, and wherein at least one of said D1 and D2 having said general Formula IIa or IIb, respectively, is being such that said electron donating atom is phosphorus and either said Z1 and Z2 or said Z3 and Z4 substituents of said phosphorous are each independently a substituted or non-substituted aryl.
11 more elements
A combinatorial library of tridentate ligands, the library comprising a plurality of compounds having the general Formula I:
- wherein:
- n is an integer from 1 to 4;
- R1-R4 are each independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl, heteroaryl, heteroalicyclic, alkoxy, thioalkoxy, hydroxy, thiol, amine, nitro and cyano;
- R5 is a leaving group capable of being dissociated so as to form a carbanion;
- D1 is an electron donating group of the general Formula IIa:
- Z1Z2Xa Formula IIa;
- and
- D2 is an electron donating group of the general Formula IIb:
- Z3Z4Xb Formula IIb;
- whereas:
- Xa and Xb are each independently an electron donating atom;
- and
- Z1, Z2, Z3 and Z4 are each independently absent or a substituent selected from the group consisting of substituted or non-substituted aryl, substituted or non-substituted alkyl, substituted or non-substituted alkoxy and substituted or non-substituted aryloxy, or, alternatively, at least two of Z1, Z2, R1 and R2 and/or at least two of Z3, Z4, R3 and R4 from together a five- or six-membered heteroalicyclic or heteroaromatic ring,
- wherein each of said electron donating atoms Xa and Xb is independently selected from the group consisting of phosphorous, sulfur, nitrogen and carbon, said carbon being a carbene that forms a part of a N-heteroalicyclic or a N-heteroaryl,
- and wherein at least one of said D1 and D2 having said general Formula IIa or IIb, respectively, is being such that said electron donating atom is phosphorus and either said Z1 and Z2 or said Z3 and Z4 substituents of said phosphorus are each independently a substituted or non-substituted aryl,
- said compounds being different from one another in at least one of said electron donating groups D1 and D2 and/or at least one of said n and R1-R5.
13 more elements
A combinatorial library of organometallic complexes, the library comprising a plurality of organometallic complexes having general Formula V:
- wherein:
- n is said integer from 1 to 4;
- R1-R4 are each independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl, heteroaryl, heteroalicyclic, alkoxy, thioalkoxy, hydroxy, thiol, amine, halogen, nitro and cyano;
- M is said transition metal;
- and
- D1 is said electron donating group of the general Formula IIa:
- Z1Z2Xa Formula IIa;
- and
- D2 is an electron donating group of the general Formula IIb:
- Z3Z4Xb Formula IIb;
- whereas:
- Xa and Xb are each independently said electron donating atom;
- and
- Z1, Z2, Z3 and Z4 are each independently absent or a substituent selected from the group consisting of substituted or non-substituted aryl, substituted or non-substituted alkyl, substituted or non-substituted alkoxy and substituted or non-substituted aryloxy, or, alternatively, at least two of Z1, Z2, R1 and R2 and/or at least two of Z3, Z4, R3 and R4 from together a five- or six-membered heteroalicyclic or heteroaromatic ring,
- wherein each of said electron donating atoms Xa and Xb is independently selected from the group consisting of phosphorous, sulfur, nitrogen and carbon, said carbon being a carbene that forms a part of a N-heteroalicyclic or a N-heteroaryl,
- and wherein at least one of said D1 and D2 having said general Formula IIa or IIb, respectively, is being such that said electron donating atom is phosphorus and either said Z1 and Z2 or said Z3 and Z4 substituents of said phosphorus are each independently a substituted or non-substituted aryl,
- said complexes being different from one another in at least one of said metal, said electron donating groups D1 and D2 and at least one of said n and R1-R5.
14 more elements
Dependencies are inferred from the claim text.