Dioxygen-triggered oxidative cleavage of the C-S bond towards C-N bond formation

被引：9

作者：

Lv, Zongchao ^{[1
]}

Wang, Huamin ^{[1
]}

Quan, Zhicong ^{[1
]}

Gao, Yuan ^{[1
]}

Lei, Aiwen ^{[1
,2
]}

机构：

[1] Wuhan Univ, Coll Chem & Mol Sci, Inst Adv Studies, Wuhan 430072, Hubei, Peoples R China

[2] Jiangxi Normal Univ, Natl Res Ctr Carbohydrate Synth, Nanchang 330022, Jiangxi, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 82期

基金：

中国国家自然科学基金;

关键词：

PALLADIUM-CATALYZED AMINATION; CARBON-SULFUR; COOPERATIVE CATALYSIS; EFFICIENT SYNTHESIS; METAL-COMPLEXES; ACTIVATION; FUNCTIONALIZATION; COBALT; BENZOXAZOLES; CYCLIZATION;

D O I：

10.1039/c9cc05707b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Research on the cleavage of C-C bonds has been well developed. By comparison with this, the activation of C-S bonds remains challenging. Herein, dioxygen-triggered oxidative cleavage of C-S bonds has been achieved, delivering a series of N-containing heterocyclic compounds that are frequently found in pesticides and pharmaceuticals. Additionally, the potential utility of this protocol was further demonstrated by a gram-scale experiment. Mechanistically, dioxygen plays a key role in the cleavage of C-S bonds towards C-N bond formation.

引用

页码：12332 / 12335

页数：4

共 50 条

[41] Photoinduced C-S Bond Cleavage of Thioglycosides and Glycosylation
Mao, Run-Ze
Guo, Fan
Xiong, De-Cai
Li, Qin
Duan, Jinyou
Ye, Xin-Shan
ORGANIC LETTERS, 2015, 17 (22) : 5606 - 5609
[42] A Convenient Method for Cleavage of Amide C-N Bond
Wei, Yingfei
Shi, Daxing
Wei, Zhen
Xu, Juan
Li, Jiarong
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (06) : 1126 - 1130
[43] CLEAVAGE OF C-S BOND DURING OXIDATION OF THIOL
COLE, ER
CHEMISTRY & INDUSTRY, 1957, (46) : 1511 - 1511
[44] C-S BOND-CLEAVAGE REACTIONS OF SULFONEDIIMINES
HAAKE, M
JURGLER, W
SPREEMANN, R
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1994, 95-6 (1-4): : 315 - 316
[45] C-S bond cleavage by a polyketide synthase domain
Ma, Ming
Lohman, Jeremy R.
Liu, Tao
Shen, Ben
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2015, 112 (33) : 10359 - 10364
[46] Formation of a nickel(II) complex with a new N2S2 macrocyclic ligand by C-Cl bond cleavage and C-S bond formation
Kawamoto, T
Kuma, H
Kushi, Y
CHEMICAL COMMUNICATIONS, 1996, (18) : 2121 - 2122
[47] Oxidative C-C bond formation and C-N bond cleavage catalyzed by complexes of copper(i) with acridine based (E N E) pincers (E = S/Se), recyclable as a catalyst
Gupta, Sonu
Dubey, Pooja
Singh, Ajai K.
Jain, Nidhi
DALTON TRANSACTIONS, 2019, 48 (27) : 10129 - 10137
[48] Towards aryl C-N bond formation in dynamic thin films
Gandy, Michael N.
Raston, Colin L.
Stubbs, Keith A.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (26) : 4594 - 4597
[49] Unexpected C-C bond cleavage of -nitroketone in the presence of TsNBr2: A new pathway for C-N bond formation
Sarma, Manas Jyoti
Phukan, Prodeep
SYNTHETIC COMMUNICATIONS, 2016, 46 (03) : 257 - 262
[50] Nitrogenation of Amides via C-C and C-N Bond Cleavage
Zhu, Ming -Hui
Cheng, Zengrui
Wei, Jialiang
Tan, Hui
Jiao, Ning
CCS CHEMISTRY, 2023, 5 (05): : 1061 - 1068

← 1 2 3 4 5 →