Synthesis 2017; 49(08): 1707-1745
DOI: 10.1055/s-0036-1589482
review
© Georg Thieme Verlag Stuttgart · New York

Organobismuth Reagents: Synthesis, Properties and Applications in Organic Synthesis

Alexandre Gagnon*
Département de chimie, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, Québec, H3C 3P8, Canada   Email: [email protected]
,
Julien Dansereau
Département de chimie, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, Québec, H3C 3P8, Canada   Email: [email protected]
,
Adrien Le Roch
Département de chimie, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, Québec, H3C 3P8, Canada   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 03 October 2016

Accepted after revision: 16 November 2016

Publication Date:
02 March 2017 (online)


Abstract

Organobismuth compounds are organometallic reagents that contain a C–Bi bond. These species, which are easily accessed from inexpensive and low-toxicity inorganic bismuth salts, are highly attractive in synthesis due to their unique properties and reactivity. A wide diversity of geometries have been found for organobismuth compounds, depending on the oxidation state of the bismuth, its charge, and the number of coordinated elements. Compounds where the bismuth bears a –1 charge (organobismuthate), a +1 (bismuthonium cation) and a +2 charge (bismuthonium dication) have been reported. Due to the presence of a lone pair, trivalent organobismuthines can act as Lewis bases in transition-metal complexes. In addition, organobismuth compounds can act as Lewis acids by forming hypervalent interactions with ligands and metals. Organobismuth compounds have been used as catalysts and reagents in a plethora of reactions. In this review, the synthesis and properties of organobismuth reagents and their use in organic reactions are reviewed.

1 Introduction

2 Synthesis of Trivalent Organobismuthines

3 Synthesis of Pentavalent Organobismuth Compounds

4 Structure, Hypervalency and Chirality

5 C-, N-, O- and S-Arylation Reactions

6 Palladium-Catalyzed Reactions

7 Other Reactions Involving Organobismuth Reagents

8 Conclusion

 
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