γ,δ,ε-C(sp3)-H Functionalization through Directed Radical H-Abstraction

被引：105

作者：

Liu, Tao ^{[1
]}

Mei, Tian-Sheng ^{[1
]}

Yu, Jin-Quan ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 18期

关键词：

ALPHA-AMINO-ACIDS; PALLADIUM-CATALYZED ARYLATION; C(SP(3))-H BONDS; PHOTOCHEMICAL REACTION; ALKOXY RADICALS; ALKYLATION; LIGAND; OLEFINATION; ACTIVATION; SP(2);

D O I：

10.1021/jacs.5b02065

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Aliphatic amides are selectively functionalized at the gamma- and delta-positions through directed radical 1,5 and 1,6 H-abstractions, respectively, The initially gamma- or delta-lactams are intercepted. by N-iodosuccinimide and trimethylsilyl azide, leading to double and triple C-H functionalizations at the gamma, delta-, and epsilon-positions. This new reactivity is exploited to convert alkyls into amino alcohols and allylic amines.

引用

页码：5871 / 5874

页数：4

共 50 条

[1] Radical Enantioselective C(sp3)-H Functionalization
Lu, Qingquan
Glorius, Frank
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (01) : 49 - 51
[2] Cyclization Through Dual C(sp3)-H Functionalization
Sadeghi, Masoud
ADVANCED SYNTHESIS & CATALYSIS, 2024,
[3] Fe-Catalyzed Regioselective C(sp3)-H-Abstraction by Tertiary Cyclopropyl Radicals
Liu, Canxiang
Feng, Tingting
Wu, Xinxin
Zhu, Chen
ACS CATALYSIS, 2023, 13 (13) : 8394 - 8401
[4] Recent progress in the radical α-C(sp3)-H functionalization of ketones
Li, Jiao-Zhe
Zhang, Wei-Kang
Ge, Guo-Ping
Zheng, Hongxing
Wei, Wen-Ting
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (34) : 7333 - 7347
[5] Method for the β-selective radical C(sp3)–H functionalization of silanes
Nature Synthesis, 2025, 4 (2): : 152 - 153
[6] C-centered radical-initiated cyclization by directed C(sp3)-H oxidative functionalization
Li, Jiao-Zhe
Mei, Lan
Yu, Xuan-Chi
Wang, Ling-Tao
Cai, Xue-Er
Li, Ting
Wei, Wen-Ting
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (20) : 5726 - 5757
[7] C(sp3)-H functionalization with isocyanides
Wang, Weixiang
Liu, Tianqi
Ding, Chang-Hua
Xu, Bin
Organic Chemistry Frontiers, 2021, 8 (13) : 3525 - 3542
[8] C(sp3)-H functionalization with isocyanides
Wang, Weixiang
Liu, Tianqi
Ding, Chang-Hua
Xu, Bin
ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (13): : 3525 - 3542
[9] Iron-Catalyzed Directed C(sp2)-H and C(sp3)-H Functionalization with Trimethylaluminum
Shang, Rui
Ilies, Laurean
Nakamura, Eiichi
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (24) : 7660 - 7663
[10] Radical C(sp3)–H functionalization and cross-coupling reactions
Dung L. Golden
Sung-Eun Suh
Shannon S. Stahl
Nature Reviews Chemistry, 2022, 6 : 405 - 427

← 1 2 3 4 5 →