Synlett 2017; 28(05): 515-520
DOI: 10.1055/s-0036-1589841
synpacts
© Georg Thieme Verlag Stuttgart · New York

Copper-Mediated Oxidative α-Arylation of Carbonyl Compounds with Boronic Acid Derivatives

Patrick J. Moon, Rylan J. Lundgren*
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Publikationsverlauf

Received: 30. November 2016

Accepted: 13. Dezember 2016

Publikationsdatum:
12.Januar 2017 (eFirst)

Abstract

We have developed copper-promoted oxidative carbon–­carbon bond-forming reactions to synthesize α-aryl carbonyl compounds. The use of weak C–H acids as nucleophiles under Chan–Evans–Lam-type conditions enables α-arylation reactivity complementary to that of established copper- or palladium-catalyzed cross-coupling methodologies that employ aryl (pseudo)halides. This Synpacts article will discuss key observations and experimental parameters that allowed for reaction development, substrate scope studies, and applications in bioactive molecule synthesis and functionalization.

1 Introduction

2 Oxidative Cross-Coupling of Activated Methylenes and Organo­boron Reagents

3 Decarboxylative Oxidative Arylation of Malonic Acid Derivatives

4 Conclusion