Synthesis 2018; 50(22): 4413-4428
DOI: 10.1055/s-0037-1610273
paper
© Georg Thieme Verlag Stuttgart · New York

The Directed ortho Metalation (DoM)–Cross-Coupling Connection: Synthesis of Polyfunctional Biaryls

Claude A. Quesnelle
,
Victor Snieckus*
We are grateful to NSERC Canada, Discovery Grant (DG 05698) for support of our synthetic programs. C.A.Q. thanks NSERC for a graduate fellowship.
Further Information

Publication History

Received: 09 July 2018

Accepted after revision: 21 August 2018

Publication Date:
05 October 2018 (online)


Dedicated to Scott Denmark, a man for all seasons in organic chemistry.

Published as part of the Special Section dedicated to Scott E. Denmark on the occasion of his 65th birthday.

Abstract

A comparative evaluation of the combined directed ortho metalation (DoM)–Suzuki–Miyaura and DoM–Negishi cross-coupling reactions with aryl triflates for the synthesis of substituted biaryls is described. Both ortho-zinc and ortho-boron aryl directed metalation group (DMG = CON(i-Pr)2, OCONEt2, OMOM, NHBoc) substrates were evaluated. The superiority of the DoM–Negishi over the DoM–Suzuki–Miyaura reaction in operational convenience and mild reaction conditions is noted. Orthogonal Negishi and Suzuki–Miyaura with Corriu–Kumada reactions for the synthesis of a teraryl derivative is also reported.

Supporting Information

 
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