Metal-Catalyzed Allylation
of Organoboranes and Organoboronic Acids

F. Christopher Pigge

doi:10.1055/s-0029-1218756

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Synthesis 2010(11): 1745-1762
DOI: 10.1055/s-0029-1218756

REVIEW

Metal-Catalyzed Allylation of Organoboranes and Organoboronic Acids

F. Christopher Pigge*
Department of Chemistry, University of Iowa, Iowa City, IA 52242, USA
Fax: +1(319)3351270; e-Mail: chris-pigge@uiowa.edu;

Further Information

Publication History

Received 14 February 2010
Publication Date:
28 April 2010 (online)

Abstract
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Abstract

Metal-catalyzed transformations have emerged as indispensable tools for carbon-carbon bond formation in contemporary synthetic chemistry. Metal-promoted cross-couplings and metal-catalyzed allylations represent two of the most widely used reaction types. However, cross-coupling reactions involving allylic electrophiles have not been extensively explored. This review presents an overview of efforts aimed at developing metal-catalyzed allylation reactions between allylic alcohol derivatives and alkenyl or aryl organoboron compounds, leading to 1,4-dienes and allylic arenes, respectively. Particular emphasis is given to regio- and stereoselective allylation procedures.

1 Introduction

2 Allylations Proceeding through π-Allyl Intermediates

2.1 Palladium Catalyzed

2.2 Nickel Catalyzed

2.3 Rhodium Catalyzed

3 Formal S_N2′-Type Allylations

3.1 Palladium Catalyzed

3.2 Rhodium Catalyzed

4 Conclusions and Future Directions

Key words

allylation - boron - cross-coupling - palladium - rhodium

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