Decarbonylative C-H Coupling of Azoles and Aryl Esters: Unprecedented Nickel Catalysis and Application to the Synthesis of Muscoride A

被引：291

作者：

Amaike, Kazuma ^{[1
]}

Muto, Kei ^{[1
]}

Yamaguchi, Junichiro ^{[1
]}

Itami, Kenichiro ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Sci, Dept Chem, Nagoya, Aichi 4648602, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 33期

关键词：

CYANOBACTERIUM NOSTOC-MUSCORUM; DIRECT ARYLATION; BOND ARYLATION; DECARBOXYLATIVE ARYLATION; BENZOIC-ACIDS; REAGENTS; FUNCTIONALIZATION; HETEROARENES; HETEROCYCLES; ANHYDRIDES;

D O I：

10.1021/ja306062c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A nickel-catalyzed decarbonylative C-H biaryl coupling of azoles and aryl esters is described. The newly developed catalytic system does not require the use of expensive metal catalysts or silver- or copper-based stoichiometric oxidants. We have successfully applied this new C-H arylation reaction to a convergent formal synthesis of muscoride A.

引用

页码：13573 / 13576

页数：4

共 50 条

[1] Pd-Catalyzed Decarbonylative C-H Coupling of Azoles and Aromatic Esters
Matsushita, Kaoru
Takise, Ryosuke
Hisada, Tomoya
Suzuki, Shin
Isshiki, Ryota
Itami, Kenichiro
Muto, Kei
Yamaguchi, Junichiro
CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (17) : 2393 - 2396
[2] C-H Alkenylation of Azoles with Enols and Esters by Nickel Catalysis
Meng, Lingkui
Kamada, Yuko
Muto, Kei
Yamaguchi, Junichiro
Itami, Kenichiro
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (38) : 10048 - 10051
[3] Nickel/Copper Cooperative Catalysis Decarbonylative Heteroarylation of Aryl Anhydrides with Benzoxazoles via C-O/C-H Coupling
Wang, Cheng-Yi
Tian, Rui
Li, Jia-Xin
Zhu, Yong-Ming
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (06): : 3378 - 3385
[4] Decarbonylative organoboron cross-coupling of esters by nickel catalysis
Muto, Kei
Yamaguchi, Junichiro
Musaev, Djamaladdin G.
Itami, Kenichiro
NATURE COMMUNICATIONS, 2015, 6
[5] Decarbonylative organoboron cross-coupling of esters by nickel catalysis
Kei Muto
Junichiro Yamaguchi
Djamaladdin G. Musaev
Kenichiro Itami
Nature Communications, 6
[6] Dibenzofuran Synthesis: Decarbonylative Intramolecular C-H Arylation of Aromatic Esters
Okita, Toshimasa
Komatsuda, Masaaki
Saito, Ami N.
Hisada, Tomoya
Takahara, Tomoaki T.
Nakayama, Keito P.
Isshiki, Ryota
Takise, Ryosuke
Muto, Kei
Yamaguchi, Junichiro
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (07) : 1358 - 1361
[7] Nickel-Catalyzed Intramolecular Decarbonylative Coupling of Aryl Selenol Esters
Bai, Jin-Hua
Qi, Xiu-Juan
Sun, Wei
Yu, Tian-Yang
Xu, Peng-Fei
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (08) : 2084 - 2088
[8] Nickel-Catalyzed Decarbonylative Coupling of Aryl Esters and Arylboronic Acids
LaBerge, Nicole A.
Love, Jennifer A.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (25) : 5546 - 5553
[9] Expedient Ni-catalyzed C-H/C-H cross-dehydrogenative coupling of aryl amides with azoles
Sarkar, Tanumay
Maharana, Prabhat Kumar
Roy, Subhasish
Punniyamurthy, Tharmalingam
CHEMICAL COMMUNICATIONS, 2022, 58 (40) : 5980 - 5983
[10] Nickel-Catalyzed C-H/C-O Coupling of Azoles with Phenol Derivatives
Muto, Kei
Yamaguchi, Junichiro
Itami, Kenichiro
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (01) : 169 - 172

← 1 2 3 4 5 →