Ni-Catalyzed Defluorination for the Synthesis of gem-Difluoro-1,3-dienes and Their [4+2] Cycloaddition Reaction

被引：33

作者：

Zhou, Minqi ^{[1
]}

Zhang, Jian ^{[2
]}

Zhang, Xing-Guo ^{[1
]}

Zhang, Xingang ^{[2
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 03期

基金：

中国国家自然科学基金;

关键词：

F BOND ACTIVATION; COUPLING REACTIONS; DIFLUOROALKYLATION; FLUORINE; ALKYNES;

D O I：

10.1021/acs.orglett.8b03841

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A nickel-catalyzed defluorination of alpha-trifluoromethylated allyl/propargyl carbonates using bis(pinacolato)-diboron (B(2)pin(2)) as a reactant is described. The reaction proceeds under relatively mild reaction conditions, providing conjugated gem-difluoroalkenes in moderate to good yields. Applications of the resulting 1,1-difluoro-1,3-dienes by [4 + 2] cycloaddition reactions with maleimide led to cyclic fluorinated products efficiently.

引用

页码：671 / 674

页数：4

共 36 条

[1] An efficient method for the synthesis of gem-difluoroolefins [J].

Cao, Chun-Ru ;

Ou, Song ;

Jiang, Min ;

Liu, Jin-Tao .

TETRAHEDRON LETTERS, 2017, 58 (05) :482-485

[2] Synthesis and Metal-Catalyzed Reactions of gem-Dihalovinyl Systems [J].

Chelucci, Giorgio .

CHEMICAL REVIEWS, 2012, 112 (03) :1344-1462

[3] Nickel-Catalyzed Coupling Reactions of Alkyl Electrophiles, Including Unactivated Tertiary Halides, To Generate Carbon-Boron Bonds [J].

Dudnik, Alexander S. ;

Fu, Gregory C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (25) :10693-10697

[4] Reactions of 1,3-dibromo-1,1-difluoro compounds with 1,8-diazabicyclo[5.4.0]undec-7-ene [J].

Elsheimer, S ;

Foti, CJ ;

Bartberger, MD .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) :6252-6255

[5] Transition-Metal (Cu, Pd, Ni)-Catalyzed Difluoroalkylation via Cross-Coupling with Difluoroalkyl Halides [J].

Feng, Zhang ;

Xiao, Yu-Lan ;

Zhang, Xingang .

ACCOUNTS OF CHEMICAL RESEARCH, 2018, 51 (09) :2264-2278

[6] Transition-Metal-Mediated and -Catalyzed C-F Bond Activation by Fluorine Elimination [J].

Fujita, Takeshi ;

Fuchibe, Kohei ;

Ichikawa, Junji .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (02) :390-402

[7] Catalytic defluorinative [3+2] cycloaddition of trifluoromethylalkenes with alkynes via reduction of nickel(II) fluoride species [J].

Fujita, Takeshi ;

Arita, Tomohiro ;

Ichitsuka, Tomohiro ;

Ichikawa, Junji .

DALTON TRANSACTIONS, 2015, 44 (45) :19460-19463

[8] Catalysis for fluorination and trifluoromethylation [J].

Furuya, Takeru ;

Kamlet, Adam S. ;

Ritter, Tobias .

NATURE, 2011, 473 (7348) :470-477

[9] Nickel-Catalyzed Stereoselective Diarylation of Alkenylarenes [J].

Gao, Pin ;

Chen, Liang-An ;

Brown, M. Kevin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (34) :10653-10657

[10] Tandem Difluoroalkylation-Arylation of Enamides Catalyzed by Nickel [J].

Gu, Ji-Wei ;

Min, Qiao-Qiao ;

Yu, Ling-Chao ;

Zhang, Xingang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (40) :12270-12274

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