Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 27, Pages 9792-9796Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja504797x
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Funding
- NSF under the CCI Center for Selective C-H Functionalization [CHE-1205646]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1205646] Funding Source: National Science Foundation
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The influence of sterically demanding dirhodium tetracarboxylate catalysts on the site selectivity of C-H functionalization by means of rhodium carbene-induced C-H insertion is described. The established dirhodium tetraprolinate-catalyzed reactions of aryldiazoacetates cause preferential C-H functionalization of secondary C-H bonds as a result of competing steric and electronic effects. The sterically more demanding dirhodium tetrakis(triarylcyclopropanecarboxylate) catalysts, exemplified by dirhodium tetrakis[(R)-(1-(biphenyl)-2,2-diphenylcyclopropanecarboxylate)] [Rh-2(R-BPCP)(4)], favor C-H functionalization of activated primary C-H bonds. Highly site-selective and enantioselective C-H functionalization of a variety of simple substrates containing primary benzylic, allylic, and methoxy C-H bonds was achieved with this catalyst. The utility of this approach has been demonstrated by the late-stage primary C-H functionalization of (-)-alpha-cedrene and a steroid.
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