Selective Nickel- and Manganese-Catalyzed Decarboxylative Cross Coupling of Some α,β-Unsaturated Carboxylic Acids with Cyclic Ethers

被引：38

作者：

Zhang, Jia-Xiang ^{[1
]}

Wang, Yan-Jing ^{[2
]}

Zhang, Wei ^{[1
]}

Wang, Nai-Xing ^{[1
]}

Bai, Cui-Bing ^{[1
]}

Xing, Ya-Lan ^{[1
]}

Li, Yi-He ^{[1
]}

Wen, Jia-Long ^{[1
]}

机构：

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

[2] Beijing Univ Chem Technol, Coll Sci, Beijing 100029, Peoples R China

来源：

SCIENTIFIC REPORTS | 2014年 / 4卷

关键词：

C-H BONDS; ALLYLIC ALKYLATION; HYDROGEN-PEROXIDE; ALDOL REACTION; ARYL BROMIDES; ALPHA; ALKENYLATION; FUNCTIONALIZATION; OLEFINATION; OXYALKYLATION;

D O I：

10.1038/srep07446

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

A nickel- and manganese-catalyzed decarboxylative cross coupling of alpha,beta-unsaturated carboxylic acids with cyclic ethers such as tetrahydrofuran and 1, 4-dioxane was developed. Oxyalkylation was achieved when nickel acetate was used as catalyst, while manganese acetate promoted the reaction of alkenylation.

引用

页数：5

共 51 条

[1] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[2] The enantioselective Tsuji allylation [J].

Behenna, DC ;

Stoltz, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15044-15045

[3] Asymmetric allylic alkylation of ketone enolates: An asymmetric claisen surrogate [J].

Burger, EC ;

Tunge, JA .

ORGANIC LETTERS, 2004, 6 (22) :4113-4115

[4] 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

[5] Copper-catalyzed decarboxylative alkenylation of sp3 C-H bonds with cinnamic acids via a radical process [J].

Cui, Zili ;

Shang, Xiaojie ;

Shao, Xiang-Feng ;

Liu, Zhong-Quan .

CHEMICAL SCIENCE, 2012, 3 (09) :2853-2858

[6] Coinage metal catalyzed C-H bond functionalization of hydrocarbons [J].

Diaz-Requejo, M. Mar ;

Perez, Pedro J. .

CHEMICAL REVIEWS, 2008, 108 (08) :3379-3394

[7] Salen-manganese complexes as catalytic scavengers of hydrogen peroxide and cytoprotective agents: structure-activity relationship studies [J].

Doctrow, SR ;

Huffman, K ;

Marcus, CB ;

Tocco, G ;

Malfroy, E ;

Adinolfi, CA ;

Kruk, H ;

Baker, K ;

Lazarowych, N ;

Mascarenhas, J ;

Malfroyt, B .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (20) :4549-4558

[8] Alkynylation of C-H bonds via reaction with acetylenic triflones [J].

Gong, JC ;

Fuchs, PL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (18) :4486-4487

[9]

Gooβen, 2008, ANGEW CHEM, V120, P3144, DOI DOI 10.1002/ANGE.200704782

[10]

Goossen LJ, 2002, ANGEW CHEM INT EDIT, V41, P1237, DOI 10.1002/1521-3773(20020402)41:7<1237::AID-ANIE1237>3.0.CO

← 1 2 3 4 5 6 →