Addition of Metalloid Hydrides to Alkynes: Hydrometallation with Boron, Silicon, and Tin

Barry M. Trost; Zachary T. Ball

doi:10.1055/s-2005-861874

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Synthesis 2005(6): 853-887
DOI: 10.1055/s-2005-861874

REVIEW

Addition of Metalloid Hydrides to Alkynes: Hydrometallation with Boron, Silicon, and Tin

Barry M. Trost*, Zachary T. Ball
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA
Fax: +1(650)7250002; e-Mail: bmtrost@stanford.edu;

Further Information

Publication History

Received 9 September 2004
Publication Date:
17 March 2005 (online)

Abstract
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Abstract

This review covers the synthesis of isolabile vinylmetalloids through hydroboration, hydrosilylation, and hydrostannation, with special focus on recent developments, metal-catalyzed reactions, and synthetically useful methods.

1 Introduction
2 Mechanistic Aspects of Hydrometallation
2.1 Hydroboration
2.2 Hydrosilylation
2.3 Hydrostannation
3 Terminal Alkynes
3.1 Hydroboration of Terminal Alkynes
3.2 Hydrosilylation of Terminal Alkynes
3.3 Hydrostannation of Terminal Alkynes
4 Internal Alkynes
4.1 Hydroboration of Internal Alkynes
4.2 Hydrosilylation of Internal Alkynes
4.3 Hydrostannation of Internal Alkynes
5 Conclusion

Key words

hydroboration - hydrostannation - hydrosilylation - alkyne - organometallic reagent

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