Practical metal-free C(sp(3))-H functionalization: construction of structurally diverse α-substituted N-benzyl and N-allyl carbamates

Zhiyu Xie; Lei Liu; Wenfang Chen; Hongbo Zheng; Qingqing Xu; Huiqing Yuan; Hongxiang Lou

doi:10.1002/anie.201310193

Practical metal-free C(sp(3))-H functionalization: construction of structurally diverse α-substituted N-benzyl and N-allyl carbamates

Angew Chem Int Ed Engl. 2014 Apr 7;53(15):3904-8. doi: 10.1002/anie.201310193. Epub 2014 Mar 5.

Authors

Zhiyu Xie¹, Lei Liu, Wenfang Chen, Hongbo Zheng, Qingqing Xu, Huiqing Yuan, Hongxiang Lou

Affiliation

¹ Key Lab of Chemical Biology of Ministry of Education, School of Pharmaceutical Sciences, Shandong University, Jinan 250012 (China) http://www.pharm.sdu.edu.cn/szdw/Liu%20lei/3/Liu_02/index.htm.

PMID: 24596320
DOI: 10.1002/anie.201310193

Abstract

Described is a practical and universal CH functionalization of readily removable N-benzyl and N-allyl carbamates, with a wide range of nucleophiles at ambient temperature promoted by Ph3 CClO4 . 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 CH compounds). The synthetic utility in target- as well as diversity-oriented syntheses is demonstrated.

Keywords: CH functionalization; antitumor agents; nitrogen heterocycles; organoboranes; synthetic methods.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbamates / chemistry*
Catalysis
Molecular Structure

Substances

Carbamates
allyl carbamate