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

Claude A. Quesnelle; Victor Snieckus

doi:10.1055/s-0037-1610273

Synthesis, Table of Contents

Synthesis 2018; 50(22): 4413-4428
DOI: 10.1055/s-0037-1610273

paper

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

Claude A. Quesnelle

,

Victor Snieckus*

Abstract

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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 65^th 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.

Key words

Suzuki–Miyaura coupling - Negishi coupling - cross-coupling - directed ortho metalation

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References

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