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A nickel catalyst for the addition of organoboronate esters to ketones and aldehydes.
Org Lett. 2009 Oct 01; 11(19):4410-3.OL

Abstract

A Ni(cod)(2)/IPr catalyst promotes the intermolecular 1,2-addition of arylboronate esters to unactivated aldehydes and ketones. Diaryl, alkyl aryl, and dialkyl ketones show good reactivity under mild reaction conditions (< or = 80 degrees C, nonpolar solvents, no strong base or acid additives). A dramatic ligand effect favors either carbonyl addition (IPr) or C-OR cross-coupling (PCy(3)) 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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Publisher Full Text (DOI)

Authors+Show Affiliations

Bouffard J
Department of Chemistry, Graduate School of Science, Nagoya University, Nagoya 464-8602, Japan.
Itami K
No affiliation info available

MeSH

AlcoholsAldehydesBoronic AcidsCatalysisCyclizationEstersKetonesMolecular StructureNickelOrganometallic CompoundsOxidation-ReductionStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19708680

Citation

Bouffard, Jean, and Kenichiro Itami. "A Nickel Catalyst for the Addition of Organoboronate Esters to Ketones and Aldehydes." Organic Letters, vol. 11, no. 19, 2009, pp. 4410-3.
Bouffard J, Itami K. A nickel catalyst for the addition of organoboronate esters to ketones and aldehydes. Org Lett. 2009;11(19):4410-3.
Bouffard, J., & Itami, K. (2009). A nickel catalyst for the addition of organoboronate esters to ketones and aldehydes. Organic Letters, 11(19), 4410-3. https://doi.org/10.1021/ol9017613
Bouffard J, Itami K. A Nickel Catalyst for the Addition of Organoboronate Esters to Ketones and Aldehydes. Org Lett. 2009 Oct 1;11(19):4410-3. PubMed PMID: 19708680.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A nickel catalyst for the addition of organoboronate esters to ketones and aldehydes. AU - Bouffard,Jean, AU - Itami,Kenichiro, PY - 2009/8/28/entrez PY - 2009/8/28/pubmed PY - 2009/12/16/medline SP - 4410 EP - 3 JF - Organic letters JO - Org Lett VL - 11 IS - 19 N2 - A Ni(cod)(2)/IPr catalyst promotes the intermolecular 1,2-addition of arylboronate esters to unactivated aldehydes and ketones. Diaryl, alkyl aryl, and dialkyl ketones show good reactivity under mild reaction conditions (< or = 80 degrees C, nonpolar solvents, no strong base or acid additives). A dramatic ligand effect favors either carbonyl addition (IPr) or C-OR cross-coupling (PCy(3)) with aryl ether substrates. A Ni(0)/Ni(II) catalytic cycle initiated by the oxidative cyclization of the carbonyl substrate is proposed. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19708680/A_nickel_catalyst_for_the_addition_of_organoboronate_esters_to_ketones_and_aldehydes_ L2 - https://doi.org/10.1021/ol9017613 DB - PRIME DP - Unbound Medicine ER -