Regiodivergent Cross-Dehydrogenative Coupling of Pyridines and Benzoxazoles: Discovery of Organic Halides as Regio-Switching Oxidants

被引：59

作者：

Yamada, Shuya ^{[1
,2
]}

Murakami, Kei ^{[1
,2
]}

Itami, Kenichiro ^{[1
,2
,3
]}

机构：

[1] Nagoya Univ, Inst Transformat Biomol WPI ITbM, Chikusa Ku, Nagoya, Aichi 4648602, Japan

[2] Nagoya Univ, Grad Sch Sci, Chikusa Ku, Nagoya, Aichi 4648602, Japan

[3] Nagoya Univ, ERATO, JST,Itami Mol Nanocarbon Project, Chikusa Ku, Nagoya, Aichi 4648602, Japan

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 10期

关键词：

C-H FUNCTIONALIZATION; DIRECT ARYLATION; C3-SELECTIVE ARYLATION; SELECTIVE ALKENYLATION; BOND ADDITION; PD CATALYSTS; N-OXIDES; HETEROARENES SCOPE; DIRECT ALKYLATION; ACTIVATION;

D O I：

10.1021/acs.orglett.6b00932

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cross-dehydrogenative coupling (CDC) of two unfunctionalized heteroarenes has been recognized as an ideal transformation to synthesize privileged heterobiaryl scaffolds. However, regioselective activation and transformation of a specific set of two heterocyclic C-H bonds among other bonds have been extremely challenging. Thus, discovering a new controlling element to achieve regio-controlled and regiodivergent heterocyclic CDCs is considered crucial. In this Letter, the unprecedented use of organic halides as an oxidant to achieve the CDC reaction of pyridines and benzoxazoles with palladium catalyst is described. Moreover, the regioselectivity of the pyridine functionalization site can be controlled by the choice of organic halides.

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收藏

页码：2415 / 2418

页数：4

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共 85 条

[1] Cobalt-Catalyzed C4-Selective Direct Alkylation of Pyridines [J].

Andou, Takashi ;

Saga, Yutaka ;

Komai, Hirotomo ;

Matsunaga, Shigeki ;

Kanai, Motomu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (11) :3213-3216

[2] Rh(I)-Catalyzed Direct Arylation of Pyridines and Quinolines [J].

Berman, Ashley M. ;

Lewis, Jared C. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) :14926-+

[3] Regiocontrolled aerobic oxidative coupling of indoles and benzene using Pd catalysts with 4,5-diazafluorene ligands [J].

Campbell, Alison N. ;

Meyer, Eric B. ;

Stahl, Shannon S. .

CHEMICAL COMMUNICATIONS, 2011, 47 (37) :10257-10259

[4] A solution to the 2-pyridyl organometallic cross-coupling problem:: Regioselective catalytic direct arylation of pyridine N-oxides [J].

Campeau, LC ;

Rousseaux, S ;

Fagnou, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18020-18021

[5] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].

Chen, Xiao ;

Engle, Keary M. ;

Wang, Dong-Hui ;

Yu, Jin-Quan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115

[6] Palladium-catalyzed C-H functionalization of pyridine N-oxides:: Highly selective alkenylation and direct arylation with unactivated arenes [J].

Cho, Seung Hwan ;

Hwang, Seung Jun ;

Chang, Sukbok .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9254-+

[7] Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].

Cho, Seung Hwan ;

Kim, Ji Young ;

Kwak, Jaesung ;

Chang, Sukbok .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083

[8] Role of Mono-N-protected Amino Acid Ligands in Palladium(II)-Catalyzed Dehydrogenative Heck Reactions of Electron-Deficient (Hetero)arenes: Experimental and Computational Studies [J].

Cong, Xuefeng ;

Tang, Huarong ;

Wu, Chao ;

Zeng, Homing .

ORGANOMETALLICS, 2013, 32 (21) :6565-6575

[9] Palladium-Catalyzed Minisci Reaction with Simple Alcohols [J].

Correia, Camille A. ;

Yang, Luo ;

Li, Chao-Jun .

ORGANIC LETTERS, 2011, 13 (17) :4581-4583

[10] Pd-catalyzed C3-selective arylation of pyridines with phenyl tosylates [J].

Dai, Fenglin ;

Gui, Qingwen ;

Liu, Jidan ;

Yang, Zhiyong ;

Chen, Xiang ;

Guo, Ruqing ;

Tan, Ze .

CHEMICAL COMMUNICATIONS, 2013, 49 (41) :4634-4636

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