Rare-Earth Y(OTf)3 Catalyzed Coupling Reaction of Ethers with Azaarenes

被引：25

作者：

Wu, Yue-Hua ^{[1
,2
]}

Wang, Nai-Xing ^{[1
,2
]}

Zhang, Tong ^{[1
,2
]}

Zhang, Lei-Yang ^{[1
,2
]}

Gao, Xue-Wang ^{[1
,2
]}

Xu, Bao-Cai ^{[3
]}

Xing, Yalan ^{[4
]}

Chi, Jian-Yi ^{[5
]}

机构：

[1] Chinese Acad Sci, Tech Inst Phys & Chem, Beijing 100190, Peoples R China

[2] Chinese Acad Sci, Univ Chinese Acad Sci, Beijing 100190, Peoples R China

[3] Beijing Technol & Business Univ, Sch Food & Chem Engn, Beijing 100048, Peoples R China

[4] William Paterson Univ New Jersey, Dept Chem, Wayne, NJ 07470 USA

[5] Chinese Acad Sci, Baotou Rare Earth Res & Dev Ctr, Baotou 014010, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 18期

基金：

中国国家自然科学基金; 国家重点研发计划;

关键词：

DIRECT ALKYNYLATION; CYCLIC ETHERS; C(SP(3))-H; BOND; ALKYLATION; ESTERIFICATION; ACTIVATION; ALPHA; ACIDS;

D O I：

10.1021/acs.orglett.9b02763

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rare-earth catalysis has become a hot topic in the field of catalytic organic reaction. Chain ethers mostly have lower reactivity and lower boiling points which limited their reaction scope. Herein, we found a rare-earth Y(OTf)(3) can catalyze the coupling reaction of ethers especially chain ethers and thioethers with azaarenes. This protocol features simple operations, a broad substrate scope (31 examples), moderate to good yields (up to 85%), and atom economy.

引用

页码：7450 / 7454

页数：5

共 39 条

[1] Direct Alkynylation of Indole and Pyrrole Heterocycles [J].

Brand, Jonathan P. ;

Charpentier, Julie ;

Waser, Jerome .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) :9346-9349

[2] Transition-Metal-Free BF3-Mediated Oxidative and Non-Oxidative Cross-Coupling of Pyridines [J].

Chen, Quan ;

Leon, Thierry ;

Knochel, Paul .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (33) :8746-8750

[3] CuBr-Mediated Oxyalkylation of Vinylarenes under Aerobic Conditions via Cleavage of sp3 C-H Bonds α to Oxygen [J].

Cheng, Kai ;

Huang, Lehao ;

Zhang, Yuhong .

ORGANIC LETTERS, 2009, 11 (13) :2908-2911

[4] Use of N-protected amino acids in the minisci radical alkylation [J].

Cowden, CJ .

ORGANIC LETTERS, 2003, 5 (23) :4497-4499

[5] Lewis Acid Catalyzed Stereoselective Dearomative Coupling of Indolylboron Ate Complexes with Donor-Acceptor Cyclopropanes and Alkyl Halides [J].

Das, Saikat ;

Daniliuc, Constantin G. ;

Studer, Armido .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (15) :4053-4057

[6] Sc(OTf)3-Catalyzed Direct Alkylation of Quinolines and Pyridines with Alkanes [J].

Deng, Guojun ;

Li, Chao-Jun .

ORGANIC LETTERS, 2009, 11 (05) :1171-1174

[7] Formal Inverse Sonogashira Reaction: Direct Alkynylation of Arenes and Heterocycles with Alkynyl Halides [J].

Dudnik, Alexander S. ;

Gevorgyan, Vladimir .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (12) :2096-2098

[8] Minisci reactions: Versatile CH-functionalizations for medicinal chemists [J].

Duncton, Matthew A. J. .

MEDCHEMCOMM, 2011, 2 (12) :1135-1161

[9] Transition-Metal-Catalyzed C-H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds [J].

Hummel, Joshua R. ;

Boerth, Jeffrey A. ;

Ellman, Jonathan A. .

CHEMICAL REVIEWS, 2017, 117 (13) :9163-9227

[10] Cu-catalyzed oxidative Povarov reactions between N-alkyl N-methylanilines and saturated oxa- and thiacycles [J].

Kawade, Rahul Kisan ;

Huple, Deepak B. ;

Lin, Rong-Jing ;

Liu, Rai-Shung .

CHEMICAL COMMUNICATIONS, 2015, 51 (30) :6625-6628

← 1 2 3 4 →