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. 2009 Apr 2;11(7):1511-4.
doi: 10.1021/ol900103a.

Application of Daugulis copper-catalyzed direct arylation to the synthesis of 5-aryl benzotriazepines

Sirilata Yotphan  1 , Robert G Bergman, Jonathan A Ellman
Affiliations

Application of Daugulis copper-catalyzed direct arylation to the synthesis of 5-aryl benzotriazepines

Sirilata Yotphan et al. Org Lett. .

Abstract

A method for the direct arylation of benzotriazepines is reported, employing an aryl iodide as the coupling partner, copper iodide as the catalyst, and lithium tert-butoxide as the base. A variety of electron-rich, electron-poor, and sterically hindered aryl iodides are compatible with the reaction conditions. The arylation reaction can also be performed outside a glovebox in air without a significant decrease in yield. Furthermore, convenient microwave conditions for carrying out this transformation are reported.

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Figures

Scheme 1
Scheme 1
Benzotriazepine Direct Arylation Substrate Scopea a Conditions: benzotriazepine substrate (1 equiv), aryl iodide (3 equiv), CuI (20 mol %), LiOtBu (2 equiv). Reported yields are isolated yields. Yields in parentheses are isolated yield when employing 1 equiv of CuI.
Scheme 2
Scheme 2
Arylation Reaction Outside of Glovebox.
See this image and copyright information in PMC

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