PdII-Catalyzed Highly Selective Arylation of Allyl Esters via C-H Functionalization of Unreactive Arenes with Retention of the Traditional Leaving Group

被引：40

作者：

Pan, Delin ^{[2
]}

Yu, Miao ^{[1
]}

Chen, Wei ^{[3
]}

Jiao, Ning ^{[2
]}

机构：

[1] Chinese Peoples Liberat Army Gen Hosp, Dept Radiol, Beijing 100853, Peoples R China

[2] Peking Univ, State Key Lab Nat & Biomimet Drugs, Sch Pharmaceut Sci, Beijing 100191, Peoples R China

[3] Chinese PLA Postgrad Med Sch, Beijing 100853, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2010年 / 5卷 / 05期

基金：

美国国家科学基金会;

关键词：

allylic compounds; heck reaction; palladium; regioselectivity; silver; OXIDATIVE HECK REACTIONS; ARYLBORONIC ACIDS; BASE-FREE; ORGANOMETALLIC CHEMISTRY; PALLADIUM(II) CATALYSIS; COUPLING REACTIONS; ROOM-TEMPERATURE; BOND FORMATION; ARYL HALIDES; OLEFINS;

D O I：

10.1002/asia.200900558

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly selective Fujiwara-Moritani oxidative Heck reaction of allyl esters with unreactive arenes via C - H bond activation was developed, in which -H elimination is highly chemo-, regio- and stereoselective. Moreover, even electron-deficient arenes are tolerated in this type of C - H activation. © 2010 Wiley-VCH Verlag GmbH © Co. KGaA, Weinheim.

引用

页码：1090 / 1093

页数：4

共 50 条

[21] A Highly Selective Amidation of Azoxybenzenes with Sulfonamides via Rhodium(III)-Catalyzed C-H Activation [J].

Li, Hongji ;

Deng, Hong .

SYNTHESIS-STUTTGART, 2017, 49 (12) :2711-2720

[22] Suzuki-Miyaura coupling reaction by PdII-catalyzed aromatic C-H bond activation directed by an N-alkyl acetamino group [J].

Shi, Zhangjie ;

Li, Bijie ;

Wan, Xiaobing ;

Cheng, Jiang ;

Fang, Zhao ;

Cao, Bin ;

Qin, Changming ;

Wang, Yang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5554-5558

[23] Highly selective directed arylation reactions via back-to-back dehydrogenative C-H borylation/arylation reactions [J].

Keske, Eric C. ;

Moore, Brandon D. ;

Zenkina, Olena V. ;

Wang, Ruiyao ;

Schatte, Gabriele ;

Crudden, Cathleen M. .

CHEMICAL COMMUNICATIONS, 2014, 50 (69) :9883-9886

[24] Direct β-Selective Styrylation of BODIPY Dyes via Palladium(II)-Catalyzed C-H Functionalization [J].

Wang, Jun ;

Wu, Qinghua ;

Gong, Qingbao ;

Cheng, Kai ;

Liu, Qingyun ;

Yu, Changjiang ;

Hao, Erhong ;

Jiao, Lijuan .

ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (04) :769-777

[25] Highly Efficient Synthesis of Arylpyrrole Derivatives via Rh(III)-Catalyzed Direct C-H Arylation with Aryl Boronic Acids [J].

Wang, Liang ;

Li, Zhan ;

Qu, Xing ;

Peng, Wangming .

CHINESE JOURNAL OF CHEMISTRY, 2015, 33 (09) :1015-1018

[26] Preparative Synthesis of Highly Substituted Tetrahydropyridines via a Rh(I)-Catalyzed C-H Functionalization Sequence [J].

Mesganaw, Tehetena ;

Ellman, Jonathan A. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2014, 18 (09) :1105-1109

[27] Palladium-Catalyzed Double C-H Functionalization of Arenes at the Positions ortho and meta to Their Directing Group: Concise Synthesis of Benzocyclobutenes [J].

Nanjo, Takeshi ;

Tsukano, Chihiro ;

Takemoto, Yoshiji .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2016, 64 (09) :1384-1392

[28] Palladium(II)-Catalyzed Direct Alkenylation and Arylation of Arenes: Removable 2-Pyridylsulfinyl Group Assisted C-H Bond Activation [J].

Yu, Ming ;

Liang, Zunun ;

Wang, Yongyong ;

Zhang, Yuhong .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (12) :4987-4994

[29] Heteroatom-Guided, Palladium-Catalyzed, Site-Selective C-H Arylation of 4H-Chromenes: Diastereoselective Assembly of the Core Structure of Myristinin B through Dual C-H Functionalization [J].

Pawar, Govind Goroba ;

Tiwari, Virendra Kumar ;

Jena, Himanshu Sekhar ;

Kapur, Manmohan .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (27) :9905-9911

[30] Nickel-catalyzed C-H arylation of benzoxazoles and oxazoles: Benchmarking the influence of electronic, steric and leaving group variations in phenolic electrophiles [J].

Steinberg, Deborah F. ;

Turk, Morgan C. ;

Kalyani, Dipannita .

TETRAHEDRON, 2017, 73 (16) :2196-2209

← 1 2 3 4 5 →