One-pot synthesis of diarylalkynes using palladium-catalyzed Sonogashira reaction and decarboxylative coupling of sp carbon and sp2 carbon

被引：270

作者：

Moon, Jeongju ^{[1
]}

Jeong, Miso ^{[1
]}

Nam, Hyungoog ^{[1
]}

Ju, Jinhun ^{[1
]}

Moon, Joong Ho ^{[2
]}

Jung, Hyun Min ^{[3
]}

Lee, Sunwoo ^{[1
]}

机构：

[1] Chonnam Natl Univ, Dept Chem, Kwangju 500757, South Korea

[2] ICx Nomad Inc, Cambridge, MA 02142 USA

[3] Korea Res Inst Chem Technol, Adv Mat Div, Taejon 305600, South Korea

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 05期

关键词：

D O I：

10.1021/ol703130y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Decarboxylative coupling of sp-sp(2) carbons is possible by palladium catalyst. Employing propiolic acid (1) as a difunctional alkyne, and using the consecutive reactions of the Sonogashira reaction and the decarboxylative coupling, unsymmetrically substituted diaryl alkynes were obtained in moderate to good yield.

引用

页码：945 / 948

页数：4

共 50 条

[31] One-pot synthesis of carbazoles by palladium-catalyzed N-arylation and oxidative coupling
Watanabe, Toshiaki
Inuki, Shinsuke
Ueda, Satoshi
Oishi, Shinya
Ohno, Hiroaki
Fujii, Nobutaka
DRUGS OF THE FUTURE, 2007, 32 : 136 - 137
[32] Palladium-Catalyzed Regioselective Oxidative Coupling of Indoles and One-Pot Synthesis of Acetoxylated Biindolyls
Liang, Zuijun
Zhao, Jinlong
Zhang, Yuhong
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (01): : 170 - 177
[33] Synthesis of Diarylalkynes by Iron/Copper Co-Catalyzed Decarboxylative sp-sp2 Coupling of Alkynyl Carboxylic Acids and Aryl Halides
Li, Tingyi
Qu, Xiaoming
Zhu, Yan
Sun, Peng
Yang, Hailong
Shan, Yuqin
Zhang, Hongxin
Liu, Defu
Zhang, Xiang
Mao, Jincheng
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (14-15) : 2731 - 2738
[34] One-Pot Palladium-Catalyzed Synthesis of Benzo[b]carbazolediones
Hoang Huy Do
Hung Quang Tran
Ohlendorf, Lars
Thang Ngoc Ngo
Tuan Thanh Dang
Ehlers, Peter
Villinger, Alexander
Langer, Peter
SYNLETT, 2015, 26 (17) : 2429 - 2433
[35] One-Pot Palladium-Catalyzed Borrowing Hydrogen Synthesis of Thioethers
Corma, Avelino
Navas, Javier
Rodenas, Tania
Sabater, Maria J.
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (51) : 17464 - 17471
[36] Ligand-Free Iron-Catalyzed Carbon(sp2)-Carbon(sp2) Cross-Coupling of Alkenyllithium with Vinyl Halides
Liu, Qiang
Wang, Zhi-Yong
Peng, Xiao-Shui
Wong, Henry N. C.
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (12): : 6325 - 6333
[37] Synthesis of 3-(Diarylmethylene)oxindoles via a Palladium-Catalyzed One-Pot Reaction: Sonogashira-Heck-Suzuki-Miyaura Combined Reaction
Dong, Guang Ri
Park, Sunhwa
Lee, Dahye
Shin, Kye Jung
Seo, Jae Hong
SYNLETT, 2013, 24 (15) : 1993 - 1997
[38] Ni-catalyzed C(sp2)-carbon and C(sp2)-heteroatom cross-coupling reactions
Li, Z
Fu, Y
Liu, L
Guo, QX
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2005, 25 (12) : 1508 - 1529
[39] Palladium-Catalyzed One-Pot Cross-Coupling of Phenols Using Nonafluorobutanesulfonyl Fluoride
Ikawa, Takashi
Saito, Kozumo
Akai, Shuji
SYNLETT, 2012, (15) : 2241 - 2246
[40] Stereospecific Palladium-Catalyzed Decarboxylative C(sp3)-C(sp2) Coupling of 2,5-Cyclohexadiene-1-carboxylic Acid Derivatives with Aryl Iodides
Chou, Chih-Ming
Chatterjee, Indranil
Studer, Armido
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) : 8614 - 8617

← 1 2 3 4 5 →