Pd-catalyzed gem-difluoroallylation of arylboronic acids with γ,γ-difluoroallylic acetates

被引：34

作者：

Zhang, Bo ^{[1
]}

Zhang, Xingang ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 06期

基金：

中国国家自然科学基金;

关键词：

ARYL BORONIC ACIDS; NUCLEOPHILIC-SUBSTITUTION; REDUCTIVE ELIMINATION; PALLADIUM; INHIBITORS; BOND; ALPHA; ALPHA-DIFLUOROKETONES; DERIVATIVES; COMPLEXES; FLUORINE;

D O I：

10.1039/c5cc08394j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly regio- and stereo-selective palladium-catalyzed gem-difluoroallylation of arylboronic acids with gamma,gamma-difluoroallylic acetates has been described. The method allows the synthesis of a variety of gem-difluoroallylated arenes with a tosyloxy group on the C=C double bond, thus providing a good opportunity for down-stream transformations.

引用

页码：1238 / 1241

页数：4

共 50 条

[41] Pd/TEMPO-catalyzed electrooxidative synthesis of biaryls from arylboronic acids or arylboronic esters [J].

Mitsudo, Koichi ;

Shiraga, Takuya ;

Kagen, Daisuke ;

Shi, Deqing ;

Becker, James Y. ;

Tanaka, Hideo .

TETRAHEDRON, 2009, 65 (40) :8384-8388

[42] Sulfur-Ligand/Pd-Catalyzed Cross-Coupling Reactions of Aryl Halides with Arylboronic Acids Under Aerobic Conditions [J].

Hong-ling Li ;

Zhi-sheng Wu ;

Min Yang ;

Yan-xing Qi .

Catalysis Letters, 2010, 137 :69-73

[43] Sulfur-Ligand/Pd-Catalyzed Cross-Coupling Reactions of Aryl Halides with Arylboronic Acids Under Aerobic Conditions [J].

Li, Hong-ling ;

Wu, Zhi-sheng ;

Yang, Min ;

Qi, Yan-xing .

CATALYSIS LETTERS, 2010, 137 (1-2) :69-73

[44] Pd(II)-catalyzed regioselective direct arylation of uracil via oxidative Heck reaction using arylboronic acids [J].

Mondal, Biplab ;

Hazra, Somjit ;

Roy, B. .

TETRAHEDRON LETTERS, 2014, 55 (05) :1077-1081

[45] Z-Selective Synthesis of γ,δ-Unsaturated Ketones via Pd-Catalyzed Ring Opening of 2-Alkylenecyclobutanones with Arylboronic Acids [J].

Zhou, Yao ;

Rao, Changqing ;

Song, Qiuling .

ORGANIC LETTERS, 2016, 18 (16) :4000-4003

[46] Indazolium halides as efficient ligands for Pd-catalyzed Suzuki-Miyaura cross-coupling of aryl bromides with arylboronic acids [J].

Chen, Qian ;

Mao, Zhuqing ;

Guo, Fang ;

Liu, Xiaoshuang .

TETRAHEDRON LETTERS, 2016, 57 (33) :3735-3738

[47] Pd-catalyzed asymmetric allylic alkylation of N-hydroxyphthalimide esters with allyl acetates [J].

Zheng, Yixuan ;

Deng, Xinhao ;

Zhao, Fei ;

Peng, Yuanyuan ;

Yan, Qiongjiao ;

Wang, Wei ;

Chen, Fener ;

Zhou, Hui .

ORGANIC CHEMISTRY FRONTIERS, 2025, 12 (05) :1537-1542

[48] Pd-Catalyzed Umpolung Chemistry of Glycal Acetates and Their [2,3]-Dehydrosugar Isomers [J].

Lee, Juyeol ;

Rhee, Young Ho .

ORGANIC LETTERS, 2022, 24 (02) :570-574

[49] Pd-Catalyzed Threefold Arylation of Baylis-Hillman Bromides and Acetates with Triarylbismuth Reagents [J].

Rao, Maddali L. N. ;

Giri, Somnath .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (24) :4580-4589

[50] Pd-Catalyzed Suzuki coupling reactions of aryl halides containing basic nitrogen centers with arylboronic acids in water in the absence of added base [J].

Li, Zhao ;

Gelbaum, Carol ;

Campbell, Zachary S. ;

Gould, Paul C. ;

Fisk, Jason S. ;

Holden, Bruce ;

Jaganathan, Arvind ;

Whiteker, Gregory T. ;

Pollet, Pamela ;

Liotta, Charles L. .

NEW JOURNAL OF CHEMISTRY, 2017, 41 (24) :15420-15432

← 1 2 3 4 5 →