Pd-Catalyzed Carbonylative Carboperfluoroalkylation of Alkynes. Through-Space 13C-19F Coupling as a Probe for Configuration Assignment of Fluoroalkyl-Substituted Olefins

被引：26

作者：

Domanski, Sylwester ^{[1
]}

Staszewska-Krajewska, Olga ^{[1
]}

Chaladaj, Wojciech ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, Kasprzaka 44-52, PL-01224 Warsaw, Poland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 15期

关键词：

COPPER-MEDIATED DIFLUOROMETHYLATION; PERFLUOROALKYL IODIDES; RADICAL-ADDITION; ALKYL IODIDES; VINYL IODIDES; TRIFLUOROMETHYLATION; ALKENES; ARYLDIFLUOROALKYLATION; CONSTANTS; HALIDES;

D O I：

10.1021/acs.joc.7b01236

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A four-component Pd-catalyzed protocol for direct synthesis of perfluoroalkyl-substituted enones is reported. Under mild conditions and low catalyst loading, alkynes, iodoperfluoroalkanes, (hetero)arylboronic acids, and carbon monoxide are assembled into highly elaborate products with good yields and excellent regio- and stereoselectivities. The configuration of the products was confirmed by the observation of through-space C-13-F-19 couplings, accessible through the analysis of routine C-13 NMR spectra.

引用

页码：7998 / 8007

页数：10

共 45 条

[1] Design and preparation of new palladium precatalysts for C-C and C-N cross-coupling reactions [J].

Bruno, Nicholas C. ;

Tudge, Matthew T. ;

Buchwald, Stephen L. .

CHEMICAL SCIENCE, 2013, 4 (03) :916-920

[2] The Palladium-Catalyzed Trifluoromethylation of Vinyl Sulfonates [J].

Cho, Eun Jin ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2011, 13 (24) :6552-6555

[3] Hydrotrifluoromethylation and iodotrifluoromethylation of alkenes and alkynes using an inorganic electride as a radical generator [J].

Choi, Sungkyu ;

Kim, Ye Ji ;

Kim, Sun Min ;

Yang, Jung Woon ;

Kim, Sung Wng ;

Cho, Eun Jin .

NATURE COMMUNICATIONS, 2014, 5

[4] Copper-Mediated Oxidative Trifluoromethylation of Boronic Acids [J].

Chu, Lingling ;

Qing, Feng-Ling .

ORGANIC LETTERS, 2010, 12 (21) :5060-5063

[5] A Broadly Applicable Method for Pd-Catalyzed Carboperfluoro-alkylation of Terminal and Internal Alkynes: A Convenient Route to Tri- and Tetrasubstituted Olefins [J].

Domanski, Sylwester ;

Chaladaj, Wojciech .

ACS CATALYSIS, 2016, 6 (06) :3452-3456

[6] AIBN-initiated radical addition of gem-difluorinated alkyl iodides to alkynes and the Pd-catalyzed Sonogashira coupling reaction of E-phenyl difluoromethylene vinylic iodides with terminal alkynes [J].

Fang, Xiang ;

Yang, Xueyan ;

Yang, Xianjin ;

Mao, Shenjie ;

Wang, Zhonghua ;

Chen, Guorong ;

Wu, Fanhong .

TETRAHEDRON, 2007, 63 (43) :10684-10692

[7] A General Synthesis of Fluoroalkylated Alkenes by Palladium-Catalyzed Heck-Type Reaction of Fluoroalkyl Bromides [J].

Feng, Zhang ;

Min, Qiao-Qiao ;

Zhao, Hai-Yang ;

Gu, Ji-Wei ;

Zhang, Xingang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (04) :1270-1274

[8] Copper-Mediated Difluoromethylation of Aryl and Vinyl Iodides [J].

Fier, Patrick S. ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (12) :5524-5527

[9] Recent Developments in the Trifluoromethylation of Alkynes [J].

Gao, Pin ;

Song, Xian-Rong ;

Liu, Xue-Yuan ;

Liang, Yong-Min .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (21) :7648-7661

[10]

Groult H., 2016, Modern Synthesis Processes and Reactivity of Fluorinated Compounds: Progress in Fluorine Science

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