Issue 38, 2016

Auxiliary-assisted palladium-catalyzed halogenation of unactivated C(sp3)–H bonds at room temperature

Abstract

The direct transformation of unactivated C(sp3)–H bonds into C-halogen bonds was achieved by palladium catalysis at room temperature with good functional group tolerance. Some drugs and natural products were readily modified by this method. Merged with substitution reaction, newly formed C–X bonds can be transformed into diverse C–O, C–S, C–C and C–N bonds. A preliminary mechanism study demonstrates that solvent is crucial for C–H activation and the C–H activation step is involved in the rate-limiting step. An isolated Pd(II) intermediate can be transformed into a halogenated product with the retention of conformation which suggests that concerted reductive elimination from Pd(IV) to form a C–X bond was favored.

Graphical abstract: Auxiliary-assisted palladium-catalyzed halogenation of unactivated C(sp3)–H bonds at room temperature

Supplementary files

Article information

Article type
Communication
Submitted
10 Jan 2016
Accepted
07 Apr 2016
First published
07 Apr 2016

Chem. Commun., 2016,52, 6423-6426

Auxiliary-assisted palladium-catalyzed halogenation of unactivated C(sp3)–H bonds at room temperature

X. Yang, Y. Sun, T. Sun and Y. Rao, Chem. Commun., 2016, 52, 6423 DOI: 10.1039/C6CC00234J

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