Sequential insertion of carbon monoxide and imines into nickel-methyl bonds: A new route to imine hydroacylation

Jason L. Davis; Bruce A. Arndtsen

doi:10.1021/om000685b

Sequential insertion of carbon monoxide and imines into nickel-methyl bonds: A new route to imine hydroacylation

Jason L. Davis, Bruce A. Arndtsen

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33 Scopus citations

Abstract

The sequential insertion of carbon monoxide and imines has been achieved at ambient temperatures with cationic nickel complexes, yielding the nickel-chelated amides (bipy)Ni[η²-C(H)TolN(R)COCH₃]⁺X^-(bipy = 2,2′-bipyridyl; Tol = p-tolyl; R = alkyl, aryl; X = OTf, PF₆, SbF₆, B(3,5-C₆H₃(CF₃)₂)₄). The addition of KCN/methanol to these products of CO/imine insertion leads to cleavage of the amide ligand, providing a facile method to achieve the overall hydroacylation of imines under mild conditions.

Original language	English (US)
Pages (from-to)	4657-4659
Number of pages	3
Journal	Organometallics
Volume	19
Issue number	23
DOIs	https://doi.org/10.1021/om000685b
State	Published - Nov 2000
Externally published	Yes

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Sequential insertion of carbon monoxide and imines into nickel-methyl bonds: A new route to imine hydroacylation",

abstract = "The sequential insertion of carbon monoxide and imines has been achieved at ambient temperatures with cationic nickel complexes, yielding the nickel-chelated amides (bipy)Ni[η2-C(H)TolN(R)COCH3]+X-(bipy = 2,2′-bipyridyl; Tol = p-tolyl; R = alkyl, aryl; X = OTf, PF6, SbF6, B(3,5-C6H3(CF3)2)4). The addition of KCN/methanol to these products of CO/imine insertion leads to cleavage of the amide ligand, providing a facile method to achieve the overall hydroacylation of imines under mild conditions.",

author = "Davis, {Jason L.} and Arndtsen, {Bruce A.}",

year = "2000",

month = nov,

doi = "10.1021/om000685b",

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T1 - Sequential insertion of carbon monoxide and imines into nickel-methyl bonds

T2 - A new route to imine hydroacylation

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AU - Arndtsen, Bruce A.

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Y1 - 2000/11

N2 - The sequential insertion of carbon monoxide and imines has been achieved at ambient temperatures with cationic nickel complexes, yielding the nickel-chelated amides (bipy)Ni[η2-C(H)TolN(R)COCH3]+X-(bipy = 2,2′-bipyridyl; Tol = p-tolyl; R = alkyl, aryl; X = OTf, PF6, SbF6, B(3,5-C6H3(CF3)2)4). The addition of KCN/methanol to these products of CO/imine insertion leads to cleavage of the amide ligand, providing a facile method to achieve the overall hydroacylation of imines under mild conditions.

AB - The sequential insertion of carbon monoxide and imines has been achieved at ambient temperatures with cationic nickel complexes, yielding the nickel-chelated amides (bipy)Ni[η2-C(H)TolN(R)COCH3]+X-(bipy = 2,2′-bipyridyl; Tol = p-tolyl; R = alkyl, aryl; X = OTf, PF6, SbF6, B(3,5-C6H3(CF3)2)4). The addition of KCN/methanol to these products of CO/imine insertion leads to cleavage of the amide ligand, providing a facile method to achieve the overall hydroacylation of imines under mild conditions.

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Sequential insertion of carbon monoxide and imines into nickel-methyl bonds: A new route to imine hydroacylation

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