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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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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