Sulfamate Esters Guide Selective Radical-Mediated Chlorination of Aliphatic C-H Bonds.

Journal Article (Journal Article)

Masked alcohols are particularly appealing as directing groups because of the ubiquity of hydroxy groups in organic small molecules. Herein, we disclose a general strategy for aliphatic γ-C(sp3 )-H functionalization guided by a masked alcohol. Specifically, we determine that sulfamate ester derived nitrogen-centered radicals mediate 1,6-hydrogen-atom transfer (HAT) processes to guide γ-C(sp3 )-H chlorination. This reaction proceeds through a light-initiated radical chain-propagation process and is capable of installing chlorine atoms at primary, secondary, and tertiary centers.

Full Text

Duke Authors

Cited Authors

  • Short, MA; Blackburn, JM; Roizen, JL

Published Date

  • January 2018

Published In

Volume / Issue

  • 57 / 1

Start / End Page

  • 296 - 299

PubMed ID

  • 29096044

Pubmed Central ID

  • 29096044

Electronic International Standard Serial Number (EISSN)

  • 1521-3773

International Standard Serial Number (ISSN)

  • 1433-7851

Digital Object Identifier (DOI)

  • 10.1002/anie.201710322


  • eng