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EP0012201A2
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Coupling of aryl and heteroaryl monochlorides
Assignee: BP Corp North America Inc
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Filing: 1979-10-29
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Granted: —
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Expires: 1999-10-29
Abstract
Abstract Aryl and heteroaryl mono chlorides are coupled in an aprotic solvent under an inert atmosphere by a catalyst mixture of a nickel compound and a ligand in the presence of a reducing metal; catalyst composition comprising a nickel compound, at least one ligand, magnesium or manganese, and a promoter.
Inventors
- 👤 Ismael Colon
- 👤 Louis Michael Maresca
- 👤 George Thomas Kwiatkowski
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-06 17:37
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/06; C07D213/22; B; B01; B01J; B01J31/00; B01J31/16; B01J31/18; B01J31/1805; B01J31/181; B01J31/1815; B01J31/24; B01J31/2404; B01J31/26; C07C; C07C1/00; C07C1/26; C07C209/00; C07C209/68; C07C41/00; C07C41/01; C07C41/18; C07C41/30; C07C43/00; C07C43/02; C07C43/20; C07C43/205; C07C43/2055; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C45/72; B01J2231/00; B01J2231/40; B01J2231/42; B01J2231/4205; B01J23/00; B01J23/02; B01J23/06; B01J23/16; B01J23/32; B01J23/34; B01J2531/00; B01J2531/80; B01J2531/84; B01J2531/847; C07C2527/00; C07C2527/06; C07C2527/08; C07C2527/10; C07C2527/128; C07C2531/00; C07C2531/16; C07C2531/24; C07C2531/26; C07C2531/28; C07C2531/30
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
168 words
A method for coupling aryl and heteroaryl mono chlorides having 4 to 30 carbons which comprises contacting said aryl mono chlorides in an aprotic solvent with a catalyst mixture comprising an anhydrous nickel compound and at least one ligand selected from the group consisting of a triaryl phosphine having 6 to about 14 carbons in each aryl moiety and an aromatic bidentate compound containing at least one ring nitrogen atom and about 5 to about 30 carbon atoms in the presence of a reducing metal selected from the group consisting of zinc, magnesium or manganese, at a temperature of about 0 to about 250°C, preferably about 25 to about 120°C wherein the ratio of gram atoms of nickel to moles of aryl chloride is in the range of about 0.0001 to about 0.5, the amount of ligand is about 0.1 to about 100 moles per gram atom of nickel and the amount of reducing metal is at least about 0.5 gram atoms per mole of reacted aryl chloride.
Claim 2
Independent Claim
168 words
A method for coupling aryl and heteroaryl mono chlorides having 4 to 30 carbons which comprises contacting said aryl mono chlorides in an aprotic solvent with a catalyst mixture comprising an anhydrous nickel compound and at least one ligand selected from the group consisting of a triaryl phosphine having 6 to about 14 carbons in each aryl moiety and an aromatic bidentate compound containing at least one ring nitrogen atom and about 5 to about 30 carbon atoms in the presence of a reducing metal selected from the group consisting of zinc, magnesium or manganese, at a temperature of about 0 to about 250°C, preferably about 25 to about 120°C wherein the ratio of gram atoms of nickel to moles of aryl chloride is in the range of about 0.0001 to about 0.5, the amount of ligand is about 0.1 to about 100 moles per gram atom of nickel and the amount of reducing metal is at least about 0.5 gram atoms per mole of reacted aryl chloride.
Claim 3
Dependent Claim
30 words
A method as claimed in claim 1 wherein the reducing metal is a finely divided powder having a mesh size of 20 or finer when measured in the U.S..sieve scale.
Claim 4
Dependent Claim
14 words
A method as claimed in claim 1 wherein the nickel compound is nickel chloride.
Claim 5
Dependent Claim
24 words
A method as claimed in claim 1 wherein the ligand is a triaryl phosphine, especially triphenyl phosphine, or an aromatic bidentate compound, especially 2,2'-bipyridine.
Claim 6
Dependent Claim
27 words
A method as claimed in claim 1 wherein the ligand is a mixture of triaryl phosphine and an aromatic bidentate compound containing at least one ring nitrogen.
Claim 7
Dependent Claim
26 words
A method as claimed in claim 1 wherein at least 0.1 moles per gram atom of nickel of an inorganic salt is added as a promoter.
Claim 8
Dependent Claim
19 words
A method as claimed in claim 6 wherein the inorganic salt is an alkali metal iodide, bromide or chloride.
Claim 9
Dependent Claim
16 words
A method as claimed in claim 1 wherein the aprotic solvent is dimethylacetamide or dimethyl formamide.
Claim 10
Dependent Claim
101 words
A method as claimed in claim 1 wherein the aryl chloride has the formula: wherein R is a monovalent inert radical selected from the group consisting of alkyl, aryl, F, unsubstituted or substituted amino,-CN, -CHO, -Oaryl, -Oalkyl, -OCOalkyl, -OCOaryl, -COOalkyl, -COOaryl, -S0 2 -alkyl, -SO 2 aryl, -S0 3 alkyl, -S0 3 aryl wherein the aryl contains 4 to about 30 carbons, the alkyl contains 1 to about 8 carbons and a is an integer having values of 0 to 4 with the proviso that no more than one R is in a position ortho to the Cl-containing ring carbon atom.
Claim 11
Dependent Claim
28 words
A method as defined in claim 9 wherein one or more of the carbon atoms of the benzene ring in formula (I) is replaced by N or P.
Claim 12
Dependent Claim
13 words
A method as claimed in claim 10 wherein the aryl chloride is 2-chloropyridine.
Claim 13
Dependent Claim
17 words
A method as claimed in claim 11 wherein R is methyl or CH3C02- and a is 1.
Claim 14
Dependent Claim
128 words
A catalyst composition comprising an anhydrous nickel compound and at least one ligand selected from the group consisting of a triaryl phosphine having 6 to about 14 carbon atoms in each aryl moiety and an aromatic bidentate compound containing at least one ring nitrogen atom and about 5 to about 30 carbon atoms, a metal selected from magnesium or manganese and a promoter selected from alkali, alkaline earth, zinc, magnesium, manganese, and aluminum halides, sulfates or phosphates, wherein the amount of ligand is about 0.1 to about 100 moles per gram atom of nickel and the amount of magnesium or manganese is at least about 1 gram atom per gram atom of nickel and the amount of promoter is at least 0.1 moles per gram atom of nickel.
Claim 15
Dependent Claim
128 words
A catalyst composition comprising an anhydrous nickel compound and at least one ligand selected from the group consisting of a triaryl phosphine having 6 to about 14 carbon atoms in each aryl moiety and an aromatic bidentate compound containing at least one ring nitrogen atom and about 5 to about 30 carbon atoms, a metal selected from magnesium or manganese and a promoter selected from alkali, alkaline earth, zinc, magnesium, manganese, and aluminum halides, sulfates or phosphates, wherein the amount of ligand is about 0.1 to about 100 moles per gram atom of nickel and the amount of magnesium or manganese is at least about 1 gram atom per gram atom of nickel and the amount of promoter is at least 0.1 moles per gram atom of nickel.
References Cited (Backward Citations)
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