Much Improved Conditions for the Negishi Cross-coupling of Iodoalanine Derived Zinc Reagents with Aryl Halides

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2009 Nov 27

PMID 19938812

Citations 27

Authors

Andrew J Ross

Hannah L Lang

Richard F W Jackson

Affiliations

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Abstract

A combination of Pd(2)(dba)(3) and SPhos (1:2 molar ratio) is an excellent precatalyst for the Negishi cross-coupling of the serine-derived organozinc reagent 2 with aryl halides, including previously difficult ortho-substituted examples. In the case of meta- and para-substituted aryl halides, Pd-loadings of 0.5 mol % give satisfactory results. Use of 2-iodoaniline as substrate gives the lactam 12 in good yield.

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