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

来源：

CHEMISTRY LETTERS | 2017年 / 46卷 / 02期

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

页码：218 / 220

页数：3

共 42 条

[21] Nickel-Catalyzed Decarbonylative Borylation of Amides: Evidence for Acyl C-N Bond Activation [J].

Hu, Jiefeng ;

Zhao, Yue ;

Liu, Jingjing ;

Zhang, Yemin ;

Shi, Zhuangzhi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (30) :8718-8722

[22] Ni-Catalyzed α-arylation of esters and amides with phenol derivatives [J].

Koch, Eva ;

Takise, Ryosuke ;

Studer, Armido ;

Yamaguchi, Junichiro ;

Itami, Kenichiro .

CHEMICAL COMMUNICATIONS, 2015, 51 (05) :855-857

[23] Nickel-Catalyzed Decarbonylative Coupling of Aryl Esters and Arylboronic Acids [J].

LaBerge, Nicole A. ;

Love, Jennifer A. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (25) :5546-5553

[24] Mechanistic Study of Chemoselectivity in Ni-Catalyzed Coupling Reactions between Azoles and Aryl Carboxylates [J].

Lu, Qianqian ;

Yu, Haizhu ;

Fu, Yao .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (23) :8252-8260

[25] Rhodium-Catalyzed C-H Bond Functionalization with Amides by Double C-H/C-N Bond Activation [J].

Meng, Guangrong ;

Szostak, Michal .

ORGANIC LETTERS, 2016, 18 (04) :796-799

[26] General Olefin Synthesis by the Palladium-Catalyzed Heck Reaction of Amides: Sterically Controlled Chemoselective N-C Activation [J].

Meng, Guangrong ;

Szostak, Michal .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (48) :14518-14522

[27] C-H Alkenylation of Azoles with Enols and Esters by Nickel Catalysis [J].

Meng, Lingkui ;

Kamada, Yuko ;

Muto, Kei ;

Yamaguchi, Junichiro ;

Itami, Kenichiro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (38) :10048-10051

[28] Palladium-Catalyzed Decarbonylative Cross-Coupling of Azinecarboxylates with Arylboronic Acids [J].

Muto, Kei ;

Hatakeyama, Taito ;

Itami, Kenichiro ;

Yamaguchi, Junichiro .

ORGANIC LETTERS, 2016, 18 (19) :5106-5109

[29] Decarbonylative organoboron cross-coupling of esters by nickel catalysis [J].

Muto, Kei ;

Yamaguchi, Junichiro ;

Musaev, Djamaladdin G. ;

Itami, Kenichiro .

NATURE COMMUNICATIONS, 2015, 6

[30] Coupling reactions of alkynylsilanes mediated by a Cu(I) salt: Novel syntheses of conjugate diynes and disubstituted ethynes [J].

Nishihara, Y ;

Ikegashira, K ;

Hirabayashi, K ;

Ando, J ;

Mori, A ;

Hiyama, T .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (06) :1780-1787

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