(Chloromethyl)magnesium Chloride-Lithium Chloride: A Chemoselective Reagent for the Synthesis of Functionalized Aromatic Chlorohydrins

Rodolfo H. V. Nishimura, Valter E. Murie, Rafael A. Soldi, Giuliano C. Clososki*

*Núcleo de Pesquisa em Produtos Naturais e Sintéticos, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Av. do Café s ̸ n, 14.040-903, Ribeirão Preto-SP, Brazil, Email: gclososkifcfrp.usp.br

R. H. V. Nishimura, V. E. Murie, R. A. Soldi, G. C. Clososki, Synthesis, 2015, 47, 1455-1460.

DOI: 10.1055/s-0034-1380288

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Abstract

The reaction of (chloromethyl)magnesium chloride-lithium chloride (ClCH₂MgCl·LiCl), a mixed lithium-magnesium carbenoid, with aromatic aldehydes bearing various functional groups enables a highly chemoselective synthesis of a range of aromatic chlorohydrins in high yields.

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Key Words

chemoselectivity, carbenoids, chlorohydrins, organometallic reagents, aldehydes, 1,2-addition

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ID: J66-Y2015