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

Sirilata Yotphan; Robert G. Bergman; Jonathan A. Ellman

doi:10.1021/ol900103a

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

Sirilata Yotphan
, Robert G. Bergman
, Jonathan A. Ellman

University of California, Berkeley

Research output: Contribution to journal › Article › peer-review

84 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1511-1514
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	7
DOIs	https://doi.org/10.1021/ol900103a
Publication status	Published - 2 Apr 2009
Externally published	Yes

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10.1021/ol900103a

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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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AU - Bergman, Robert G.

AU - Ellman, Jonathan A.

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N2 - 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.

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

Abstract

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