A nickel catalyst for the addition of organoboronate esters to ketones and aldehydes

Jean Bouffard; Kenichiro Itami

doi:10.1021/ol9017613

A nickel catalyst for the addition of organoboronate esters to ketones and aldehydes

Jean Bouffard, Kenichiro Itami

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

63 Scopus citations

Abstract

A Ni(cod)₂/IPr catalyst promotes the intermolecular 1,2-addition of arylboronate esters to unactivated aldehydes and ketones. Dlaryl, alkyl aryl, and dialkyl ketones show good reactivity under mild reaction conditions (<80° C, nonpolar solvents, no strong base or acid additives). A dramatic ligand effect favors either carbonyl addition (IPr) or C-OR cross-coupling (PCy₃) with aryl ether substrates. A Ni(0)/Ni(II) catalytic cycle initiated by the oxidative cyclization of the carbonyl substrate Is proposed.

Original language	English
Pages (from-to)	4410-4413
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	19
DOIs	https://doi.org/10.1021/ol9017613
State	Published - 1 Oct 2009

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abstract = "A Ni(cod)2/IPr catalyst promotes the intermolecular 1,2-addition of arylboronate esters to unactivated aldehydes and ketones. Dlaryl, alkyl aryl, and dialkyl ketones show good reactivity under mild reaction conditions (<80° C, nonpolar solvents, no strong base or acid additives). A dramatic ligand effect favors either carbonyl addition (IPr) or C-OR cross-coupling (PCy3) with aryl ether substrates. A Ni(0)/Ni(II) catalytic cycle initiated by the oxidative cyclization of the carbonyl substrate Is proposed.",

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AU - Itami, Kenichiro

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AB - A Ni(cod)2/IPr catalyst promotes the intermolecular 1,2-addition of arylboronate esters to unactivated aldehydes and ketones. Dlaryl, alkyl aryl, and dialkyl ketones show good reactivity under mild reaction conditions (<80° C, nonpolar solvents, no strong base or acid additives). A dramatic ligand effect favors either carbonyl addition (IPr) or C-OR cross-coupling (PCy3) with aryl ether substrates. A Ni(0)/Ni(II) catalytic cycle initiated by the oxidative cyclization of the carbonyl substrate Is proposed.

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A nickel catalyst for the addition of organoboronate esters to ketones and aldehydes

Abstract

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