Cu-Catalyzed Transformation of Alkynes and Alkenes with Azide and Dimethyl Sulfoxide Reagents

被引：77

作者：

Shen, Tao ^{[1
]}

Huang, Xiaoqiang ^{[1
]}

Liang, Yu-Feng ^{[1
]}

Jiao, Ning ^{[1
,2
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

[2] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai 200062, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 24期

基金：

中国国家自然科学基金;

关键词：

PUMMERER REACTION CHEMISTRY; FACILE SYNTHESIS; BOND FORMATION; METHYL KETONES; EFFICIENT; STRATEGY; DMSO; NITROGENATION; OXIDATION; ACCESS;

D O I：

10.1021/acs.orglett.5b03179

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and efficient Cu-catalyzed nitrogenation of alkynes and alkenes for the direct synthesis of sulfur-containing triazoles is described. Simple and readily available sulfoxides and azides are employed as the S- and N-source to prepare highly value N-,S-containing compounds from simple alkynes and alkenes.

引用

页码：6186 / 6189

页数：4

共 71 条

[1] ONE-POT ACCESS TO 3,3′-BISINDOLYLMETHANES THROUGH THE INTERMOLECULAR PUMMERER REACTION
Abe, Takumi
Ikeda, Toshiaki
Itoh, Tomoki
Hatae, Noriyuki
Toyota, Eiko
Ishikura, Minoru
[J]. HETEROCYCLES, 2014, 88 (01) : 187 - 191
[2] Highly regioselective nucleophilic carbon-carbon bond formation on furans and thiophenes initiated by Pumerer-type reaction
Akai, S
Kawashita, N
Satoh, H
Wada, Y
Kakiguchi, K
Kuriwaki, I
Kita, Y
[J]. ORGANIC LETTERS, 2004, 6 (21) : 3793 - 3796
[3] Recent advances in Pummerer reactions
Akai, Shuji
Kita, Yasuyuki
[J]. SULFUR-MEDIATED REARRANGEMENTS I, 2007, 274 : 35 - 76
[4] Oxidative Hydroxylation Mediated by Alkoxysulfonium Ions
Ashikari, Yosuke
Nokami, Toshiki
Yoshida, Jun-ichi
[J]. ORGANIC LETTERS, 2012, 14 (03) : 938 - 941
[5] Integrated Electrochemical-Chemical Oxidation Mediated by Alkoxysulfonium Ions
Ashikari, Yosuke
Nokami, Toshiki
Yoshida, Jun-ichi
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (31) : 11840 - 11843
[6] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions
Beletskaya, Irina P.
Ananikov, Valentine P.
[J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1596 - 1636
[7] THE ORGANOSULFUR CHEMISTRY OF THE GENUS ALLIUM - IMPLICATIONS FOR THE ORGANIC-CHEMISTRY OF SULFUR
BLOCK, E
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1992, 31 (09) : 1135 - 1178
[8] The Pummerer reaction: Methodology and strategy for the synthesis of heterocyclic compounds
Bur, SK
Padwa, A
[J]. CHEMICAL REVIEWS, 2004, 104 (05) : 2401 - 2432
[9] Cu(II)-Mediated Methylthiolation of Aryl C-H Bonds with DMSO
Chu, Lingling
Yue, Xuyi
Qing, Feng-Ling
[J]. ORGANIC LETTERS, 2010, 12 (07) : 1644 - 1647
[10] Structure-Based Discovery of Inhibitors of Microsomal Prostaglandin E2 Synthase-1, 5-Lipoxygenase and 5-Lipoxygenase-Activating Protein: Promising Hits for the Development of New Anti-inflammatory Agents
De Simone, Rosa
Chini, Maria Giovanna
Bruno, Ines
Riccio, Raffaele
Mueller, Daniela
Werz, Oliver
Bifulco, Giuseppe
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (06) : 1565 - 1575

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