Journal Article Synthesis of 3-Aryl-2-(trifluoromethyl)indoles via Copper-Catalyzed Hydroarylation and Subsequent Cadogan Cyclization

Yamamoto, Yoshihiko  ,  Ohkubo, Erina  ,  Shibuya, Masatoshi

359 ( 10 )  , pp.1747 - 1751 , 2017-05-17 , Wiley
ISSN:1615-4150
Description
The copper-catalyzed hydroarylation of (trifluoromethyl)alkynes with (o-nitrophenyl)boronic acids selectively afforded trisubstituted (trifluoromethyl)alkenes bearing an o-nitrophenyl group. The obtained hydroarylation products were converted into 3-aryl-2-(trifluoromethyl)indoles in high yields via molybdenum-catalyzed Cadogan cyclization. Similarly, the hydroarylation product prepared from (o-nitrophenyl)(trifluoromethyl)alkyne and (p-anisyl)boronic acid also underwent Cadogan cyclization, albeit with a longer reaction time, affording the desired indole product in a high yield.
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