Direct thiocyanation of ketene dithioacetals under transition-metal-free conditions

被引：73

作者：

Chen, Qiao ^{[1
]}

Lei, Yingjie ^{[1
]}

Wang, Yanfang ^{[1
]}

Wang, Chao ^{[1
]}

Wang, Yanan ^{[1
]}

Xu, Zhaoqing ^{[1
]}

Wang, Huan ^{[1
]}

Wang, Rui ^{[1
]}

机构：

[1] Lanzhou Univ, Sch Basic Med Sci, Key Lab Preclin Study New Drugs Gansu Prov, Lanzhou 730000, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2017年 / 4卷 / 03期

关键词：

ARYL THIOCYANATES; C-3; THIOCYANATION; FACILE SYNTHESIS; EFFICIENT; ACCESS; ALKENES; ROUTE; TRIFLUOROMETHYLTHIOCYANATION; THIOCYANOOXYGENATION; PALLADIUM;

D O I：

10.1039/c6qo00676k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first direct thiocyanation of ketene dithioacetals has been accomplished in the presence of N-chlorosuccinimide (NCS) and NH4SCN under transition-metal-free conditions. The operationally simple one-pot procedure, which is insensitive to air, was found to be well-tolerated by a wide range of substrates. Terminal alkenes and hydrazine were identified to be qualified candidates for the process as well. Furthermore, the product could be successfully transformed into synthetically and biologically interesting -SCF3 substituted N-heteroaromatic compounds and thiotetrazole containing compounds.

引用

页码：369 / 372

页数：4

共 50 条

[1] H2O-controlled selective thiocyanation and alkenylation of ketene dithioacetals under electrochemical oxidation
Wen, Jiangwei
Zhang, Longfei
Yang, Xiaoting
Niu, Cong
Wang, Shuangfeng
Wei, Wei
Sun, Xuejun
Yang, Jianjing
Wang, Hua
GREEN CHEMISTRY, 2019, 21 (13) : 3597 - 3601
[2] Transition-metal-free regioselective thiocyanation of phenols, anilines and heterocycles
Mete, Trimbak B.
Khopade, Tushar M.
Bhat, Ramakrishna G.
TETRAHEDRON LETTERS, 2017, 58 (05) : 415 - 418
[3] Transition-Metal-Free Approach for the Synthesis of N-Arylated Piperidones and their Ketals from Ketene Dithioacetals
Sahu, Satya Narayan
Shaw, Ranjay
Althagafi, Ismail
Pratap, Ramendra
SYNLETT, 2025, 36 (05) : 488 - 495
[4] Transition-Metal-Free Regioselective Thiocyanation of Triisopropylsilane (TIPS)-Protected Phenols
Ju Guodong
Zhou Guangyu
Zhao Yingsheng
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (04) : 1327 - 1336
[5] Transition-Metal-Free Csp2-H Regioselective Thiocyanation of Free Anilines
Dai, Peng
Li, Chenxiao
Li, Yufei
Xia, Qing
Zhang, Mingzhi
Gu, Yu-Cheng
Zhang, Wei-Hua
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (10) : 1585 - 1588
[6] Oxysulfonylation of Alkenes with Sulfonyl Hydrazides under Transition-Metal-Free Conditions
Liu, Congrong
Ding, Lianghui
Guo, Guang
Liu, Weiwei
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (05) : 910 - 912
[7] Transition-Metal-Free Direct Arylation of Anilines
Pirali, Tracey
Zhang, Fengzhi
Miller, Anna H.
Head, Jenna L.
McAusland, Donald
Greaney, Michael F.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (04) : 1006 - 1009
[8] NaHSO3-Mediated Direct Synthesis of Sulfinic Esters from Sulfonyl Hydrazides under Transition-Metal-Free Conditions
Zhang, Guofu
Fan, Qiankun
Wang, Huimin
Zhao, Yiyong
Ding, Chengrong
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (03) : 833 - 837
[9] Transition metal free, green and facile halogenation of ketene dithioacetals using a KX-oxidant system
Rai, Vishakha
Sorabad, Ganesh Shivayogappa
Maddani, Mahagundappa Rachappa
NEW JOURNAL OF CHEMISTRY, 2021, 45 (02) : 1109 - 1113
[10] Regioselective α-arylation of coumarins and 2-pyridones with phenylhydrazines under transition-metal-free conditions
Chauhan, Parul
Ravi, Makthala
Singh, Shikha
Prajapati, Prashant
Yadav, Prem P.
RSC ADVANCES, 2016, 6 (01) : 109 - 118

← 1 2 3 4 5 →