Synthesis of 5-lodo-1,2,3,4-tetrahydropyridines by Rhodium-Catalyzed Tandem Nucleophilic Attacks Involving 1-Sulfonyl-1,2,3-triazoles and Iodides

被引：41

作者：

Man, Zengming ^{[1
]}

Dai, Haican ^{[1
]}

Shi, Yinping ^{[1
]}

Yang, Dongdong ^{[1
]}

Li, Chuan-Ying ^{[1
]}

机构：

[1] Zhejiang Sci Tech Univ, Dept Chem, Hangzhou 310018, Zhejiang, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 19期

基金：

中国国家自然科学基金;

关键词：

ALPHA-DIAZOCARBONYL COMPOUNDS; OXO GOLD CARBENES; C-H INSERTION; DIAZO-COMPOUNDS; CONTROLLING SELECTIVITY; EFFICIENT SYNTHESIS; AZAVINYL CARBENES; ORGANIC-SYNTHESIS; DERIVATIVES; N-SULFONYL-1,2,3-TRIAZOLES;

D O I：

10.1021/acs.orglett.6b02428

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sodium iodide is used for the first time as a nucleophile to trap an alpha-imino rhodium carbene, which triggers a tandem process involving intermolecular nucleophilic, attack and intramolecular S(N)2 reaction. A series of 5-iodo-1,2,3,4-tetrahydtopyridines are obtained in high yield, and the synthetic utility of the products is demonstrated in cross-coupling reactions and the construction of biorelated polycyclic compounds.

引用

页码：4962 / 4965

页数：4

共 50 条

[11] Rhodium-Catalyzed Transannulation of 1,2,3-Triazoles with Nitriles
Horneff, Tony
Chuprakov, Stepan
Chernyak, Natalia
Gevorgyan, Vladimir
Fokin, Valery V.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) : 14972 - +
[12] Rhodium-catalyzed enantioselective cyclopropanation of olefins with N-sulfonyl 1,2,3-triazoles
Chuprakov, Stepan
Kwok, Sen Wai
Zhang, Li
Lercher, Lukas
Fokin, Valery V.
Journal of the American Chemical Society, 2009, 131 (50): : 18034 - 18035
[13] Rhodium-Catalyzed Enantioselective Cyclopropanation of Olefins with N-Sulfonyl 1,2,3-Triazoles
Chuprakov, Stepan
Kwok, Sen Wai
Zhang, Li
Lercher, Lukas
Fokin, Valery V.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (50) : 18034 - +
[14] Rhodium-Catalyzed Tandem Cyclopropanation/Cope Rearrangement of 4-Alkenyl-1-sulfonyl-1,2,3-triazoles with Dienes
Parr, Brendan T.
Davies, Huw M. L.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (38) : 10044 - 10047
[15] Rhodium-Catalyzed Transannulation of N-Sulfonyl-1,2,3-triazoles with Carboxylic Esters
Kaieda, Yuya
Yamamoto, Kosuke
Kuriyama, Masami
Onomura, Osamu
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (17) : 3081 - 3087
[16] Efficient, mild synthesis of N-unsubstituted 1,2,3-triazoles from methanolysis of 1-sulfonyl-1,2,3-triazoles
Rodriguez-Florencio, Janeth
Martinez-Otero, Diego
Garcia-Eleno, Marco A.
Cuevas-Yanez, Erick
SYNTHETIC COMMUNICATIONS, 2018, 48 (17) : 2189 - 2197
[17] Rhodium-Catalyzed Transannulation of 1,2,3-Triazoles to Polysubstituted Pyrroles
Rajasekar, Shanmugam
Anbarasan, Pazhamalai
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (17): : 8428 - 8434
[18] Rhodium(II)-catalyzed transannulation of 1-sulfonyl-1,2,3-triazoles with 2H-azirines: a new method to dihydropyrazines
Ding, Haixin
Hong, Sanguo
Zhang, Ning
TETRAHEDRON LETTERS, 2015, 56 (03) : 507 - 510
[19] Chiral cyclobutenes from 1-sulfonyl-1,2,3-triazoles using chiral rhodium complexes
Korthals, Keith A.
Fokin, Valery V.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
[20] Asymmetric Synthesis of Cyclopropylmethanamines by Rhodium-catalyzed Cyclopropanation of Pinacol Allylboronate with N-Sulfonyl-1,2,3-triazoles
Miura, Tomoya
Nakamuro, Takayuki
Nikishima, Hiroki
Murakami, Masahiro
CHEMISTRY LETTERS, 2016, 45 (08) : 1003 - 1005

← 1 2 3 4 5 →