Practical Metal-Free C(sp3)H Functionalization: Construction of Structurally Diverse [alpha]-Substituted N-Benzyl and N-Allyl Carbamates

Described is a practical and universal CH functionalization of readily removable N-benzyl and N-allyl carbamates, with a wide range of nucleophiles at ambient temperature promoted by Ph3CClO4. The metal-free reaction has an excellent functional-group tolerance, and displays a broad scope with respec...

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Bibliographic Details
Published in:Angewandte Chemie 2014-04, Vol.126 (15), p.3985-3989
Main Authors: Xie, Zhiyu, Liu, Lei, Chen, Wenfang, Zheng, Hongbo, Xu, Qingqing, Yuan, Huiqing, Lou, Hongxiang
Format: Article
Language:eng ; ger
Subjects:
Ambient temperature
Chemistry
Construction
Displays
Nucleophiles
Tolerances
Utilities
Online Access:Get full text
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Summary:Described is a practical and universal CH functionalization of readily removable N-benzyl and N-allyl carbamates, with a wide range of nucleophiles at ambient temperature promoted by Ph3CClO4. The metal-free reaction has an excellent functional-group tolerance, and displays a broad scope with respect to both N-carbamates and nucleophile partners (a variety of organoboranes and CH compounds). The synthetic utility in target- as well as diversity-oriented syntheses is demonstrated. [PUBLICATION ABSTRACT]
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201310193