Microwave-Promoted Synthesis of 1-Tetralones via Iminyl Radical-Mediated 1,5-Hydrogen Atom Transfer

被引：0

作者：

Jones, Spencer A. ^{[1
]}

Botello, Jesus A. ^{[1
]}

Singh, Jatinder ^{[1
]}

Damstedt, Gracie L. ^{[1
]}

Payne, Joshua C. ^{[1
]}

Griffin, Elias D. ^{[1
]}

Osayawe, Osasere J. ^{[1
]}

Castle, Steven L. ^{[1
]}

机构：

[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2025年 / 90卷 / 06期

基金：

美国国家科学基金会;

关键词：

INTRAMOLECULAR HYDROGEN ABSTRACTION; CYCLIZATION; ETHERS;

D O I：

10.1021/acs.joc.4c02887

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Microwave irradiation of O-phenyloximes produces 1-tetralones via N-O homolysis, 1,5-hydrogen atom transfer (HAT), and cyclization of a radical intermediate onto an aromatic ring. The HAT step is facilitated by coordination of Lewis acid InCl3<middle dot>H2O to an iminyl radical. The reaction is rapid and exhibits a broad substrate scope. A larger scale transformation can be performed using conventional heating instead of microwave irradiation.

引用

页码：2547 / 2552

页数：6

共 50 条

[21] Iron-Catalyzed, Iminyl Radical-Triggered Cascade 1,5-Hydrogen Atom Transfer/(5+2) or (5+1) Annulation: Oxime as a Five-Atom Assembling Unit
Liang, Wu
Jiang, Kun
Du, Fei
Yang, Jie
Shuai, Li
Ouyang, Qin
Chen, Ying-Chun
Wei, Ye
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (43) : 19222 - 19228
[22] 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
[23] RADICAL CYCLIZATION AND 1,5-HYDROGEN TRANSFER IN SELECTED AROMATIC DIAZONIUM SALTS
Maggio, Benedetta
Fontana, Gianfranco
Raffa, Demetrio
Ferrante, Francesco
Daidone, Giuseppe
HETEROCYCLES, 2014, 89 (01) : 83 - 101
[24] 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
[25] Free-radical functionalisation of β-amino alcohols via 1,5-hydrogen atom abstraction in 1,3-oxazolidines
Gosain, R
Norrish, AM
Wood, ME
TETRAHEDRON LETTERS, 1999, 40 (36) : 6673 - 6676
[26] Photoinduced Remote C(sp3)-H Imination Enabled by Vinyl Radical- Mediated 1,5-Hydrogen Atom Transfer
Li, Shan-Shan
Jiang, Yu-Shi
Luo, Xue-Ling
Pan, Cheng-Xue
Xia, Peng-Ju
ORGANIC LETTERS, 2023, : 1595 - 1599
[27] Metal-Free Photochemical Olefin Isomerization of Unsaturated Ketones via 1,5-Hydrogen Atom Transfer
Manikandan, Rajendran
Phatake, Ravindra S.
Lemcoff, N. Gabriel
CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (29)
[28] Generation of glycinyl radicals via a 1,5-hydrogen atom transfer reaction.: Applications to γ-lactam formation
Rancourt, J
Gorys, V
Jolicoeur, E
TETRAHEDRON LETTERS, 1998, 39 (30) : 5339 - 5342
[29] 1,5-Hydrogen atom transfer/radical cyclization of cycloalkanones bearing a β-iodo α,β-unsaturated ester or nitrile side chain
Sha, CK
Hsu, CW
Chen, YT
Cheng, SY
TETRAHEDRON LETTERS, 2000, 41 (50) : 9865 - 9869
[30] Metal-Free Synthesis of (E)-Vinyl Sulfones via An Insertion of Sulfur Dioxide/1,5-Hydrogen Atom Transfer Sequence
He, Fu-Sheng
Yao, Yanfang
Xie, Wenlin
Wu, Jie
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (21) : 4744 - 4748

← 1 2 3 4 5 →