Palladium-Catalyzed Atom-Transfer Radical Cyclization at Remote Unactivated C(sp3)−H Sites: Hydrogen-Atom Transfer of Hybrid Vinyl Palladium Radical Intermediates

Maxim Ratushnyy, Marvin Parasram, Yang Wang, Vladimir Gevorgyan

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

A novel mild, visible-light-induced palladium-catalyzed hydrogen atom translocation/atom-transfer radical cyclization (HAT/ATRC) cascade has been developed. This protocol involves a 1,5-HAT process of previously unknown hybrid vinyl palladium radical intermediates, thus leading to iodomethyl carbo- and heterocyclic structures.

Original languageEnglish (US)
Pages (from-to)2712-2715
Number of pages4
JournalAngewandte Chemie - International Edition
Volume57
Issue number10
DOIs
StatePublished - Mar 1 2018
Externally publishedYes

Fingerprint

Cyclization
Palladium
Hydrogen
Atoms
Charcoal

Keywords

  • cyclizations
  • hydrogen-atom transfer
  • palladium
  • photochemistry
  • radicals

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

@article{044816e1508e41e5ac393b5b5d23fc95,
title = "Palladium-Catalyzed Atom-Transfer Radical Cyclization at Remote Unactivated C(sp3)−H Sites: Hydrogen-Atom Transfer of Hybrid Vinyl Palladium Radical Intermediates",
abstract = "A novel mild, visible-light-induced palladium-catalyzed hydrogen atom translocation/atom-transfer radical cyclization (HAT/ATRC) cascade has been developed. This protocol involves a 1,5-HAT process of previously unknown hybrid vinyl palladium radical intermediates, thus leading to iodomethyl carbo- and heterocyclic structures.",
keywords = "cyclizations, hydrogen-atom transfer, palladium, photochemistry, radicals",
author = "Maxim Ratushnyy and Marvin Parasram and Yang Wang and Vladimir Gevorgyan",
year = "2018",
month = "3",
day = "1",
doi = "10.1002/anie.201712775",
language = "English (US)",
volume = "57",
pages = "2712--2715",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "10",

}

TY - JOUR

T1 - Palladium-Catalyzed Atom-Transfer Radical Cyclization at Remote Unactivated C(sp3)−H Sites

T2 - Hydrogen-Atom Transfer of Hybrid Vinyl Palladium Radical Intermediates

AU - Ratushnyy, Maxim

AU - Parasram, Marvin

AU - Wang, Yang

AU - Gevorgyan, Vladimir

PY - 2018/3/1

Y1 - 2018/3/1

N2 - A novel mild, visible-light-induced palladium-catalyzed hydrogen atom translocation/atom-transfer radical cyclization (HAT/ATRC) cascade has been developed. This protocol involves a 1,5-HAT process of previously unknown hybrid vinyl palladium radical intermediates, thus leading to iodomethyl carbo- and heterocyclic structures.

AB - A novel mild, visible-light-induced palladium-catalyzed hydrogen atom translocation/atom-transfer radical cyclization (HAT/ATRC) cascade has been developed. This protocol involves a 1,5-HAT process of previously unknown hybrid vinyl palladium radical intermediates, thus leading to iodomethyl carbo- and heterocyclic structures.

KW - cyclizations

KW - hydrogen-atom transfer

KW - palladium

KW - photochemistry

KW - radicals

UR - http://www.scopus.com/inward/record.url?scp=85042551027&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85042551027&partnerID=8YFLogxK

U2 - 10.1002/anie.201712775

DO - 10.1002/anie.201712775

M3 - Article

C2 - 29341489

AN - SCOPUS:85042551027

VL - 57

SP - 2712

EP - 2715

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 10

ER -