Palladium-catalyzed Decarbonylative Alkynylation of Aromatic Esters

被引:52
作者
Okita, Toshimasa [1 ]
Kumazawa, Kazushi [2 ,3 ]
Takise, Ryosuke [2 ,3 ]
Muto, Kei [1 ]
Itami, Kenichiro [2 ,3 ,4 ]
Yamaguchi, Junichiro [1 ]
机构
[1] Waseda Univ, Dept Appl Chem, Shinjuku Ku, 3-4-1 Ohkubo, Tokyo 1698555, Japan
[2] Nagoya Univ, Inst Transformat Biomol WPI ITbM, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[3] Nagoya Univ, Grad Sch Sci, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[4] Nagoya Univ, JST ERATO, Itami Mol Nanocarbon Project, Chikusa Ku, Nagoya, Aichi 4648602, Japan
关键词
Decarbonylative reaction; Palladium; Alkyne; HAGIHARA COUPLING REACTIONS; ARYL IODIDES; NICKEL; ALKYNYLSILANES; CHLORIDES; AZOLES; AMIDES; CHEMOSELECTIVITY; OLEFINATION; SILYLATION;
D O I
10.1246/cl.161001
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A palladium-catalyzed decarbonylative alkynylation reaction of aromatic esters with terminal alkynes is reported. This reaction allows for halogen-free Sonogashira coupling, resulting in various aryl- and heteroarylalkynes. The utility of the reaction was demonstrated by orthogonal coupling reaction.
引用
收藏
页码:218 / 220
页数:3
相关论文
共 42 条
[1]   Synthesis of Triarylpyridines in Thiopeptide Antibiotics by Using a C-H Arylation/Ring-Transformation Strategy [J].
Amaike, Kazuma ;
Itami, Kenichiro ;
Yamaguchi, Junichiro .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (13) :4384-4388
[2]   Decarbonylative C-H Coupling of Azoles and Aryl Esters: Unprecedented Nickel Catalysis and Application to the Synthesis of Muscoride A [J].
Amaike, Kazuma ;
Muto, Kei ;
Yamaguchi, Junichiro ;
Itami, Kenichiro .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13573-13576
[3]   THE PALLADIUM-CATALYZED ARYLATION OF ACTIVATED ALKENES WITH AROYL CHLORIDES [J].
BLASER, HU ;
SPENCER, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 233 (02) :267-274
[4]   The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL REVIEWS, 2007, 107 (03) :874-922
[5]   Chemicals from Alkynes with Palladium Catalysts [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL REVIEWS, 2014, 114 (03) :1783-1826
[6]   Recent advances in Sonogashira reactions [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5084-5121
[7]   Palladium-Catalyzed Sonogashira Coupling of Aryl Mesylates and Tosylates [J].
Choy, Pui Ying ;
Chow, Wing Kin ;
So, Chau Ming ;
Lau, Chak Po ;
Kwong, Fuk Yee .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (33) :9982-9985
[8]   Microwave-Promoted Copper-Free Sonogashira-Hagihara Couplings of Aryl Imidazolylsulfonates in Water [J].
Civicos, Jose F. ;
Alonso, Diego A. ;
Najera, Carmen .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (01) :203-208
[9]   Nickel-Catalyzed Decarbonylative C-H Coupling Reactions: A Strategy for Preparing Bis(heteroaryl) Backbones [J].
Correa, Arkaitz ;
Cornella, Josep ;
Martin, Ruben .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (07) :1878-1880
[10]  
Diederich Francois., 2004, ACETYLENE CHEM CHEM, V1, DOI [10.1002/3527605487, DOI 10.1002/3527605487]