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Synlett 2014; 25(10): 1350-1370
DOI: 10.1055/s-0033-1340867
DOI: 10.1055/s-0033-1340867
account
Trifluoromethylated Internal Alkynes: Versatile Building Blocks for the Preparation of Various Fluorine-Containing Molecules
Weitere Informationen
Publikationsverlauf
Received: 05. Januar 2014
Accepted after revision: 04. Februar 2014
Publikationsdatum:
11. April 2014 (online)
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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For reviews, see:
For reports on the preparation of CF3 alkynes published prior to 2000, see:
For reports on the preparation of CF3 alkynes published since 2000, see:
For other synthetic applications of CF3 alkynes, see:
It has been reported that various CF3 propargylamines can be prepared through the reaction of a CF3 acetylide with N-sulfinylimines, see:
For palladium-catalyzed carbostannylation reactions, see:
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