Synlett 2014; 25(10): 1350-1370
DOI: 10.1055/s-0033-1340867
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© Georg Thieme Verlag Stuttgart · New York

Trifluoromethylated Internal Alkynes: Versatile Building Blocks for the ­Preparation of Various Fluorine-Containing Molecules

Tsutomu Konno*
Department of Chemistry and Materials Technology, Kyoto Institute of Technology Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan   Fax: +81(75)7247517   Email: konno@kit.ac.jp
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Publication History

Received: 05 January 2014

Accepted after revision: 04 February 2014

Publication Date:
11 April 2014 (online)


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Abstract

Trifluoromethylated alkynes (CF3 alkynes) are among the most powerful synthetic intermediates for the preparation of ­fluorine-containing materials. In this account, our recent advances on the synthesis and reactions of trifluoromethylated alkynes are described.

1 Introduction

2 Synthesis of Trifluoromethylated Alkynes

3 Addition Reactions of H–M, C–M and M–M (M = Metal) with Trifluoromethylated Alkynes

3.1 Hydrostannation (H–Sn)

3.2 Hydroboration (H–B)

3.3 Hydrosilylation (H–Si)

3.4 Other Hydrometallations (H–Cu, H–Al)

3.5 Carbostannylation (C–Sn)

3.6 Carbocupration (C–Cu)

3.7 Carbopalladation (C–Pd)

3.8 Bisstannylation (Sn–Sn)

3.9 Silylstannylation (Si–Sn)

4 Cyclization Using Trifluoromethylated Alkynes

4.1 Synthesis of Trifluoromethylated Dihydroisoxazoles

4.2 Synthesis of Trifluoromethylated Indoles

4.3 Synthesis of Trifluoromethylated Benzofurans

4.4 Synthesis of Trifluoromethylated Isoquinolines

4.5 Synthesis of Trifluoromethylated Cyclopentenones

4.6 Synthesis of Trifluoromethylated Benzenes

5 Concluding Remarks

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