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

Jean Bouffard, Kenichiro Itami

Research output: Contribution to journalArticlepeer-review

61 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 languageEnglish
Pages (from-to)4410-4413
Number of pages4
JournalOrganic Letters
Volume11
Issue number19
DOIs
StatePublished - 1 Oct 2009

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