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

The direct transformation of unactivated C(sp 3 )-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...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2016-01, Vol.52 (38), p.6423-6426
Main Authors: Yang, Xinglin, Sun, Yonghui, Sun, Tian-yu, Rao, Yu
Format: Article
Language:English
Subjects:
Activation
Activation analysis
Carbon-carbon composites
Chemical bonds
Halogenation
Solvents
Tolerances
Transformations
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Summary:The direct transformation of unactivated C(sp 3 )-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. The direct transformation of unactivated C(sp 3 )-H bonds into C-halogen bonds was achieved by palladium catalysis at room temperature with good functional group tolerance.
ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc00234j