Sulfamyl Radicals Direct Photoredox-Mediated Giese Reactions at Unactivated C(3)-H Bonds.

Published

Journal Article

Alcohol-anchored sulfamate esters guide the alkylation of tertiary and secondary aliphatic C(3)-H bonds. The transformation proceeds directly from N-H bonds with a catalytic oxidant, a contrast to prior methods which have required preoxidation of the reactive nitrogen center, or employed stoichiometric amounts of strong oxidants to obtain the sulfamyl radical. These sulfamyl radicals template otherwise rare 1,6-hydrogen-atom transfer (HAT) processes via seven-membered ring transition states to enable C(3)-H functionalization during Giese reactions.

Full Text

Duke Authors

Cited Authors

  • Kanegusuku, ALG; Castanheiro, T; Ayer, SK; Roizen, JL

Published Date

  • August 2019

Published In

Volume / Issue

  • 21 / 15

Start / End Page

  • 6089 - 6095

PubMed ID

  • 31313933

Pubmed Central ID

  • 31313933

Electronic International Standard Serial Number (EISSN)

  • 1523-7052

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/acs.orglett.9b02234

Language

  • eng