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Direct Amidation of N-Boc- and N-Cbz-Protected Amines via Rhodium-Catalyzed Coupling of Arylboroxines and Carbamates

Diane S. W. Lim, Tedrick T. S. Lew and Yugen Zhang*

*Institute of Bioengineering and Nanotechnology, 31 Biopolis Way, The Nanos, Singapore 138669, Singapore, Email: ygzhangibn.a-star.edu.sg

D. S. W. Lim, T. T. S. Lew, Y. Zhang, Org. Lett., 2015, 17, 6054-6057.

DOI: 10.1021/acs.orglett.5b03061 (free Supporting Information)



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Abstract

N-Boc- and N-Cbz-protected amines can be directly converted into amides by a novel rhodium-catalyzed coupling with arylboroxines. Both protected anilines and aliphatic amines are efficiently transformed into a wide variety of secondary benzamides, including sterically hindered and electron-deficient amides. The reaction tolerates acid-labile and reducible functional groups.

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Key Words

benzamides, Boc-protected amines


ID: J54-Y2015