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US 7,608,713 B2Granted
Tertiary phosphines and their methods of preparation
AssigneeCytec Canada Inc.
InventorsChristine J. Bradaric-Baus, Yuehui Zhou
Life of this patent
Estimating the term…
Abstract
Tertiary phosphines are prepared by reacting a phosphine (PH3 or a primary or secondary phosphine) with a cyclic alpha,beta-unsaturated carbonyl compound having no more than one C═C double bond conjugated with a carbonyl group. The inventive tertiary phosphines can have R groups that are the same or different. The inventive tertiary phosphines may be used as ligands for metal catalysts or as starting materials for preparing phosphonium salts or ylids.
Claims29
A compound of formula I:
- wherein:
- RX is R1 or R3,
- Ry is R2 or R3, and
- RZ is R3;
- and wherein:
- (A) R1 and R2 have the following values:
- (i) R1 and R2 and the phosphorus atom to which R1 and R2 are bonded form a seven-to ten-membered heterobicycle;
- or
- (ii) each of R1 and R2 is independently:
- unsubstituted C1-C30 alkyl;
- substituted C1-C30 alkyl;
- unsubstituted C3-C8 cycloalkyl;
- substituted C3-C8 cycloalkyl;
- unsubstituted C2-C30 alkenyl;
- substituted C2-C30 alkenyl;
- unsubstituted C2-C30 alkynyl;
- substituted C2-C30 alkynyl;
- unsubstituted C6-C18 aryl;
- substituted C6-C18 aryl;
- unsubstituted C7-C30 aralkyl;
- substituted C7-C30 aralkyl;
- unsubstituted C2-C30 heteroalkyl containing one or two heteroatoms which are N, O or S;
- substituted C2-C30 heteroalkyl containing one or two heteroatoms which are N, O or S;
- unsubstituted C3-C8 heterocycle containing one or two heteroatoms which are N, O or S;
- substituted C3-C8 heterocycle containing one or two heteroatoms which are N, O or S;
- unsubstituted C3-C30 heteroalkenyl containing one or two heteroatoms which are N, O or S;
- substituted C3-C30 heteroalkenyl containing one or two heteroatoms which are N, O or S;
- unsubstituted C3-C30 heteroalkynyl containing one or two heteroatoms which are N, O and S;
- substituted C3-C30 heteroalkynyl containing one or two heteroatoms which are N, O and S;
- unsubstituted C6-C18 heteroaryl containing one or two heteroatoms which are N, O or S;
- substituted C6-C18 heteroaryl containing one or two heteroatoms which are N, O or S;
- unsubstituted C7-C30 heteroaralkyl containing one or two heteroatoms which are N, O or S;
- and substituted C7-C30 heteroaralkyl containing one or two heteroatoms which are N, O or S;
- and
- (B) R3 is selected from:
- with the proviso that when RX and RY are ethyl, R3 cannot be 3-oxo-cyclopentyl.
33 more elements
A compound of formula I:
- RX is R1 or R3,
- RY is R2 or R3, and
- RZ is R3,
- and wherein:
- (A) R1 and R2 have the following values:
- (i) R1 and R2 and the phosphorus atom to which R1 and R2 are bonded form a seven-to ten-membered heterobicycle;
- or
- (ii) each of R1 and R2 is independently:
- unsubstituted C1-C30 aklyl;
- substituted C1-C30 alkyl;
- unsubstituted C3-C8 cycloalkyl;
- substituted C3-C8 cycloalkyl;
- unsubstituted C2-C30 alkenyl;
- substituted C2-C30 alkenyl;
- unsubstituted C2-C30 alkynyl;
- substituted C2-C30 alkynyl;
- unsubstituted C6-C18 aryl;
- substituted C6-C18 aryl;
- unsubstituted C7-C30 aralkyl;
- substituted C7-C30 aralkyl;
- unsubstituted C2-C30 heteroalkyl containing one or two heteroatoms which are N, O or S;
- substituted C2-C30 heteroalkyl containing one or two heteroatoms which are N, O or S;
- unsubstituted C3-C8 heterocycle containing one or two heteroatoms which are N. O or S;
- substituted C3-C8 heterocycle containing one or two heteroatoms which are N, O or S;
- unsubstituted C3-C30 heteroalkenyl containing one or two heteroatoms which are N, O or S;
- substituted C3-C30 heteroalkenyl containing one or two heteroatoms which are N, O or S;
- unsubstituted C3-C30 heteroalkynyl containing one or two heteroatoms which are N, O and S;
- substituted C3-C30 heteroalkynyl containing one or two heteroatoms which are N, O and S;
- unsubstituted C6-C18 heteroaryl containing one or two heteroatoms which are N, O or S;
- substituted C6-C18 heteroaryl containing one or two heteroatoms which are N, O or S;
- unsubstituted C7-C30 heteroaralkyl containing one or two heteroatoms which are N, O or S;
- and substituted C7-C30 heteroaralkyl containing one or two heteroatoms which are N, O or S;
- and
- (B) R3 is:
31 more elements
A compound of formula I:
- wherein:
- RX is R1 or R3,
- RY is R2 or R3,and
- RZ is R3,
- and wherein:
- (A) R1 and R2 have the following values:
- (i) R1 and R2 and the phosphorus atom to which R1 and R2 are bonded form a seven-to ten-membered heterobicycle;
- or
- (ii) each of R1 and R2 is independently:
- unsubstituted C1-C30 aklyl;
- substituted C1-C30 alkyl;
- unsubstituted C3-C8 cycloalkyl;
- substituted C3-C8 cycloalkyl;
- unsubstituted C2-C30 alkenyl;
- substituted C2-C30 alkenyl;
- unsubstituted C2-C30 alkynyl;
- substituted C2 1-C30 alkynyl;
- unsubstituted C6-C18 aryl;
- substituted C6-C18 aryl;
- unsubstituted C7-C30 aralkyl;
- substituted C7-C30 aralkyl;
- unsubstituted C2-C30 heteroalkyl containing one or two heteroatoms which are N, O or S;
- substituted C2-C30 heteroalkyl containing one or two heteroatoms which are N, O or S;
- unsubstituted C3-C8 heterocycle containing one or two heteroatoms which are N. O or S;
- substituted C3-C8 heterocycle containing one or two heteroatoms which are N, O or S;
- unsubstituted C3-C30 heteroalkenyl containing one or two heteroatoms which are N, O or S;
- substituted C3-C30 heteroalkenyl containing one or two heteroatoms which are N, O or S;
- unsubstituted C3-C30 heteroalkynyl containing one or two heteroatoms which are N, O and S;
- substituted C3-C30 heteroalkynyl containing one or two heteroatoms which are N, O and S;
- unsubstituted C6-C18 heteroaryl containing one or two heteroatoms which are N, O or S;
- substituted C6-C18 heteroaryl containing one or two heteroatoms which are N, O or S;
- unsubstituted C7-C30 heteroaralkyl containing one or two heteroatoms which are N, O or S;
- and substituted C7-C30 heteroaralkyl containing one or two heteroatoms which are N, O or S;
- and
- (B) R3 is:
- with the proviso that when RX and RY are ethyl, R3 cannot be 3-oxo-cyclopentyl.
33 more elements
The compound 3-(dicyclohexylphosphino)cyclohexan-1-one.
The compound 3-(di(iso-butyl)phosphino)cycloexan-1-one.
The compound 3-(9-phosphabicyclo[3.3.1]nonan-9-yl)-cyclohexan-1-one.
The compound di(cyclohexanon-3-yl)-cyclohexylphosphine.
Dependencies are inferred from the claim text.