Rhodium-catalyzed denitrogenative thioacetalization of N-sulfonyl-1,2,3-triazoles with disulfides: an entry to diverse transformation of terminal alkynes

被引：19
作者：
Zhang, Hao [1 ]
Wang, Hui [1 ]
Yang, Haijun [1 ]
Fu, Hua [1 ]
机构：
[1] Tsinghua Univ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Minist Educ, Dept Chem, Beijing 100084, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 22期
基金：
中国国家自然科学基金;
关键词：
SOLVENT-FREE CONDITIONS; AZAVINYL CARBENES; STEREOCONTROLLED SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; EFFICIENT CATALYST; CONVENIENT REAGENT; CARBONYL-COMPOUNDS; TRANSANNULATION; 1-SULFONYL-1,2,3-TRIAZOLES; DITHIOACETALIZATION;
D O I：
10.1039/c5ob00638d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient and useful rhodium-catalyzed denitrogenative thio-acetalization of N-sulfonyl-1,2,3-triazoles has been developed for the first time. The protocol uses readily available N-sulfonyl-1,2,3-triazoles and diaryl disulfides as the starting materials. The corresponding hydrolytic and reductive products with thioacetals were obtained in good to excellent yields, and the reactions were carried out easily under mild conditions with tolerance of some functional groups. Furthermore, the generated thioacetals could be transformed into some useful compounds. Therefore, the present method provides a novel and valuable strategy for the diverse transformation of alkynes.
引用
收藏
页码：6149 / 6153
页数：5
相关论文
共 50 条
[41]   Relay Catalysis of Rh (II) and Cobaloxime: Stereoselective Synthesis of Spiroindanones from N-Sulfonyl-1,2,3-triazoles [J].
Liu, Zhao ;
Du, Qiuchen ;
Zhai, Hongbin ;
Li, Yun .
ORGANIC LETTERS, 2018, 20 (23) :7514-7517
[42]   Synthesis of Pyrroles from Terminal Alkynes, N-Sulfonyl Azides, and Alkenyl Alkyl Ethers through 1-Sulfonyl-1,2,3-triazoles [J].
Kim, Cheol-Eui ;
Park, Sangjune ;
Eom, Dahan ;
Seo, Boram ;
Lee, Phil Ho .
ORGANIC LETTERS, 2014, 16 (07) :1900-1903
[43]   Synthesis of Piperidine Derivatives by Rhodium- Catalyzed Tandem Reaction of N-Sulfonyl-1,2,3-Triazole and Vinyl Ether [J].
Yu, Sisi ;
An, Yuehui ;
Wang, Wenlin ;
Xu, Ze-Feng ;
Li, Chuan-Ying .
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (11) :2125-2130
[44]   Synthesis of Cyclopenta[b]indoles via Rhodium-Catalyzed Cascade Migration-Annulation of 1-Sulfonyl-1,2,3-triazoles and Indoles [J].
Xu, Huaping ;
Wang, Heng ;
Xu, Ze-Feng ;
Duan, Shengguo ;
Li, Chuan-Ying .
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (10) :1623-1628
[45]   Synthesis of α-(2-Hydroxyphenyl)-α-Aminoketones by Rhodium-Catalyzed Tandem Reaction of 1-Sulfonyl-1,2,3-Triazoles and Benzoquinone-Derived Alcohols [J].
Xu, Ze-Feng ;
Wang, Weipeng ;
Cen, Mengjie ;
Feng, Zijuan ;
Duan, Shengguo ;
Li, Chuan-Ying .
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (14) :2888-2893
[46]   Scope of the Reactions of Indolyl- and Pyrrolyl-Tethered N-Sulfonyl-1,2,3-triazoles: Rhodium(II)-Catalyzed Synthesis of Indole- and Pyrrole-Fused Polycyclic Compounds [J].
Fu, Liangbing ;
Davies, Huw M. L. .
ORGANIC LETTERS, 2017, 19 (07) :1504-1507
[47]   Rhodium-catalysed synthesis of fused pyrimidine derivatives employing N-sulfonyl-1,2,3-triazoles as a 1-aza-[4C] synthon [J].
Xu, Ze-Feng ;
An, Yuehui ;
Chen, Yidian ;
Duan, Shengguo .
TETRAHEDRON LETTERS, 2019, 60 (28) :1849-1853
[48]   A General Proline-Catalyzed Synthesis of 4,5-Disubstituted N-Sulfonyl-1,2,3-Triazoles from 1,3-Dicarbonyl Compounds and Sulfonyl Azide [J].
Rajasekar, Shanmugam ;
Anbarasan, Pazhamalai .
CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (24) :4563-4567
[49]   Rhodium-Catalyzed Synthesis of 2,5-Epoxybenzo[f][1,4]oxazepines by Tandem Reaction of 1-Sulfonyl-1,2,3-triazoles and Salicylaldehydes [J].
Shi, Yinping ;
Yu, Xing ;
Li, Chuan-Ying .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (29) :6429-6433
[50]   Rh(II)-Catalyzed Tandem Cyclization of Aliphatic N-Sulfonyl-1,2,3-triazoles and Alcohols for the Synthesis of 6-Alkoxy Piperidin-3-ones [J].
Zhang, Ran ;
Li, Yang ;
Ali, Arshad ;
Hao, Jiamin ;
Bi, Xihe ;
Fu, Junkai .
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (22) :4057-4061
12345