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

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

Key words

trifluoromethylated alkynes - regioselectivity - stereoselectivity - hydrometallation - carbometallation - bismetallation - cyclization

• References


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