Visible-Light-Mediated Energy Transfer Enables the Synthesis of β-Lactams via Intramolecular Hydrogen Atom Transfer

被引：23

作者：

Oddy, Meghan J. ^{[1
]}

Kusza, Daniel A. ^{[1
]}

Epton, Ryan G. ^{[2
]}

Lynam, Jason M. ^{[2
]}

Unsworth, William P. ^{[2
]}

Petersen, Wade F. ^{[1
]}

机构：

[1] Univ Cape Town, Dept Chem, ZA-7700 Cape Town, South Africa

[2] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2022年 / 61卷 / 48期

基金：

新加坡国家研究基金会;

关键词：

C-H Functionalization; Energy Transfer; Heterocycles; Hydrogen Atom Transfer; Photocatalysis; C-H FUNCTIONALIZATION; PHOTOCHEMICAL-REACTIONS; ASYMMETRIC-SYNTHESIS; ALIPHATIC-AMINES; ACTIVATION; PHOTOCYCLIZATION; PHOTOCATALYSIS; CONSTRUCTION; CYCLIZATION; AZETIDINES;

D O I：

10.1002/anie.202213086

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of 2-azetidinones (beta-lactams) from simple acrylamide starting materials by visible-light-mediated energy transfer catalysis is reported. The reaction features a C(sp(3))-H functionalization via a variation of the Norrish-Yang photocyclization involving a carbon-to-carbon 1,5-hydrogen atom transfer (supported by deuterium labelling and DFT calculations) and can be used for the construction of a diverse range of beta-lactam products.

引用

页数：6

共 50 条

[1] Synthesis of Sulfilimines via Visible-Light-Mediated Triplet Energy Transfer to Sulfonyl Azides
Arichi, Norihito
Amano, Tsuyoshi
Wu, Shuhan
Inuki, Shinsuke
Ohno, Hiroaki
CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (48)
[2] Total Synthesis of (+)-Polyoxamic Acid via Visible-Light-Mediated Photocatalytic β-Scission and 1,5-Hydrogen Atom Transfer of Glucose Derivative
Matsuoka, Takuro
Inuki, Shinsuke
Miyagawa, Takashi
Oishi, Shinya
Ohno, Hiroaki
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (12): : 8271 - 8278
[3] Visible-light-mediated synthesis of polysubstituted pyrroles via CAr-I reduction triggered 1,5-hydrogen atom transfer process
Wang, Junlei
Xie, Qinglin
Gao, Guocheng
Wei, Guofen
Wei, Xinxin
Chen, Xuemei
Zhang, Daohai
Li, Hongqing
Huang, Binbin
ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (16): : 4522 - 4528
[4] Visible-Light-Mediated Energy Transfer Enables Cyclopropanes Bearing Contiguous All-Carbon Quaternary Centers
Xia, Dingding
Wu, Rongkai
Wang, Jinxin
Han, Xinyu
Li, Yanchuan
Li, Qiannan
Luan, Xin
Hong, Xin
Zhang, Yu
Zhang, Wei-Dong
ACS CATALYSIS, 2023, 13 (14) : 9806 - 9816
[5] Visible-light-mediated deuteration of aldehydes with D2O via polarity-matched reversible hydrogen atom transfer
Dong, Jian-Yang
Xu, Wen-Tao
Yue, Fu-Yang
Song, Hong-Jian
Liu, Yu-Xiu
Wang, Qing-Min
TETRAHEDRON, 2021, 82
[6] Visible-light-mediated C(sp3)-H activation by photo induced hydrogen-atom transfer
Li, Han
Zhang, Ming-Tian
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2018, 355 : 109 - 113
[7] Peptide macrocyclisation via intramolecular interception of visible-light-mediated desulfurisation
Smith, Frances R.
Meehan, Declan
Griffiths, Rhys C.
Knowles, Harriet J.
Zhang, Peiyu
Williams, Huw E. L.
Wilson, Andrew J.
Mitchell, Nicholas J.
CHEMICAL SCIENCE, 2024, 15 (25) : 9612 - 9619
[8] Visible-Light-Mediated Radical α-C(sp3)-H gem-Difluoroallylation of Amides with Trifluoromethyl Alkenes via Halogen Atom Transfer and 1,5-Hydrogen Atom Transfer
Liu, Dan
Xiao, Fang
Ebel, Ben
Oppel, Iris M.
Patureau, Frederic W.
ORGANIC LETTERS, 2025, 27 (10) : 2377 - 2382
[9] [Copper(phenanthroline)(bisisonitrile)+-Complexes for the Visible-Light-Mediated Atom Transfer Radical Addition and Allylation Reactions
Knorn, Matthias
Rawner, Thomas
Czerwieniec, Rafal
Reiser, Oliver
ACS CATALYSIS, 2015, 5 (09): : 5186 - 5193
[10] Visible-light-induced dehydrogenation of dihydroquinolinones via the combination of energy transfer and hydrogen atom transfers
Feng, Jin
Tang, Hanguang
Guo, Hao
Ding, Aishun
ORGANIC CHEMISTRY FRONTIERS, 2025, 12 (04): : 1183 - 1188

← 1 2 3 4 5 →