Chemoselective Synthesis of Unsymmetrical Internal Alkynes or Vinyl Sulfones via Palladium-Catalyzed Cross-Coupling Reaction of Sodium Sulfinates with Alkynes

被引：101

作者：

Xu, Yanli ^{[1
]}

Zhao, Jinwu ^{[1
]}

Tang, Xiaodong ^{[1
]}

Wu, Wanqing ^{[1
]}

Jiang, Huanfeng ^{[1
]}

机构：

[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 09期

基金：

中国国家自然科学基金;

关键词：

alkynes; cross-coupling; palladium catalyst; sodium sulfinates; vinyl sulfones; ONE-POT SYNTHESIS; HYDROGEN-PEROXIDE; ARYL HALIDES; SONOGASHIRA REACTION; CARBOXYLIC-ACIDS; DIARYL SULFONES; BOND ACTIVATION; CARBON; OXIDATION; SULFIDES;

D O I：

10.1002/adsc.201300945

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A highly efficient and mild palladium-catalyzed cross-coupling of sodium sulfinates and alkynes for the selective synthesis of unsymmetrical internal alkynes and vinyl sulfones has been developed. This methodology has advantages of easily accessible starting materials, functional group tolerance and a wide range of substrates, which provides rapid access to alkynes and vinyl sulfones.

引用

页码：2029 / 2039

页数：11

共 50 条

[21] Palladium-catalyzed reductive cross-coupling between α-bromo carboxamides and terminal alkynes
Aliyu, Muinat A.
Li, Bowen
Yang, He
Tang, Wenjun
ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (21) : 3505 - 3508
[22] SYNTHESIS OF AROMATIC HETEROCYCLES VIA PALLADIUM-CATALYZED ANNULATION OF INTERNAL ALKYNES
LAROCK, RC
YUM, EK
DOTY, MJ
SHAM, KKC
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11): : 3270 - 3271
[23] Synthesis of isocoumarins and α-pyrones via palladium-catalyzed annulation of internal alkynes
Larock, RC
Doty, MJ
Han, XJ
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (24): : 8770 - 8779
[24] PALLADIUM-CATALYZED CROSS-COUPLING OF VINYL IODIDES WITH ORGANOSTANNANES: SYNTHESIS OF UNSYMMETRICAL DIVINYL KETONES.
Goure, W.F.
Wright, Michael E.
Davis, P.D.
Labadie, Sharada S.
Stille, J.K.
Journal of the American Chemical Society, 1984, 106 (21): : 6417 - 6422
[25] Efficient palladium-catalyzed homocoupling reaction and Sonogashira cross-coupling reaction of terminal alkynes under aerobic conditions
Li, JH
Liang, Y
Xie, YX
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (11): : 4393 - 4396
[26] Iridium complex-catalyzed cross-coupling reaction of terminal alkynes with internal alkynes via C-H activation of terminal alkynes
Hirabayashi, T
Sakaguchi, S
Ishii, Y
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (06) : 872 - 876
[27] Palladium-Catalyzed Denitrogenative Coupling of Aryldiazonium Salts with Terminal Alkynes for the Assembly of Internal Alkynes
Guo, Ziyang
Xiong, Xun
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (40)
[28] Synthesis of β- and γ-carbolines by the palladium-catalyzed iminoannulation of internal alkynes
Zhang, HM
Larock, RC
ORGANIC LETTERS, 2001, 3 (20) : 3083 - 3086
[29] Synthesis of indenes by the palladium-catalyzed carboannulation of internal alkynes
Zhang, DH
Yum, EK
Liu, ZJ
Larock, RC
ORGANIC LETTERS, 2005, 7 (22) : 4963 - 4966
[30] The Synthesis of Pyridyl[2.2]paracyclophanes by Palladium-Catalyzed Cross-Coupling of Pyridine Sulfinates
Mungalpara, Maulik N.
Plieger, Paul G.
Rowlands, Gareth J.
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (04) : 1069 - 1080

← 1 2 3 4 5 →