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N-Arylation of Carbamates through Photosensitized Nickel Catalysis

Leleti Rajender Reddy*, Sharadsrikar Kotturi, Yogesh Waman, Vudem Ravinder Reddy, Chirag Patel, Ajinath Kobarne, Sasikumar Kuttappan

*Piramal Discovery Solutions, Pharmaceutical Special Economic Zone, Sarkhej Bavla Highway, Ahmedabad, Gujarat 382213, India, Email: reddylrajenderyahoo.com

L. R. Reddy, S. Kotturi, Y. Waman, V. R. Reddy, C. Patel, A. Kobarne, S. Kuttappan, J. Org. Chem., 2018, 83, 13854-13860.

DOI: 10.1021/acs.joc.8b02182 (free Supporting Information)


Abstract

A highly efficient Ni(II)-catalyzed photoredox N-arylation of Cbz-amines/Boc-amines with aryl electrophiles at room temperature provides a wide variety of N-aromatic and N-heteroaromatic carbamate products that find use in the synthesis of several biologically active molecules. The reaction offers a viable alternative to traditional palladium-catalyzed Buchwald-Hartwig reaction.

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Key Words

carbamates, anilines, Cbz-protected amines, Boc-protected amines


ID: J42-Y2018