Highly regioselective C-H carbonylation of alkenes with phenyl formate via aryl to vinyl 1,4-palladium migration

被引：11

作者：

Ye, Tao ^{[1
,2
]}

Cheng, Fangyuan ^{[1
]}

Zhang, Jian ^{[1
]}

Liu, Yang-Zi ^{[1
]}

Wang, Quannan ^{[1
]}

Deng, Wei-Ping ^{[1
,2
]}

机构：

[1] Zhejiang Normal Univ, Dept Chem, Key Lab Minist Educ Adv Catalysis Mat, 688 Yingbin Rd, Jinhua 321004, Peoples R China

[2] East China Univ Sci & Technol, Shanghai Frontiers Sci Ctr Optogenet Tech Cell Met, Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 06期

关键词：

STEREOSELECTIVE-SYNTHESIS; CATALYZED CARBONYLATION; PALLADIUM; CARBOXYLATION; ACTIVATION; OLEFINS; RHODIUM; ACIDS; ALKOXYCARBONYLATION; ESTERIFICATION;

D O I：

10.1039/d3qo00066d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report herein a palladium-catalyzed C-H carbonylation of gem-disubstituted ethylenes with phenyl formate as a convenient CO surrogate through an aryl to vinyl 1,4-palladium migration, providing a wide range of beta,beta-diaryl substituted alpha,beta-unsaturated esters in high efficiency and with excellent regio- and stereoselectivities. The reaction proceeds with broad substrate scope and good functional group compatibility. The present synthetic protocol provides a convenient and powerful method to directly access a key intermediate for (Z)-tamoxifen.

引用

页码：1537 / 1543

页数：7

共 75 条

[1] DNA Compatible Intermolecular Wittig Olefination for the Construction of α, β-Unsaturated Carbonyl Compounds [J].

An, Yu-Long ;

Li, Ke ;

Shen, Yanfang ;

Hong, Zibing ;

Chen, Linlin ;

Hu, Yujing ;

Zhou, Lichun ;

Wang, Disha ;

Shi, Xiaodong ;

Liu, Shien ;

Su, Wenji ;

Cui, Weiren ;

Kuai, Letian ;

Yang, Hongfang ;

Peng, Xuanjia .

ORGANIC LETTERS, 2020, 22 (10) :3931-3935

[2] Intertwining Olefin Thianthrenation with Kornblum/Ganem Oxidations: Ene-type Oxidation to Furnish α,β-Unsaturated Carbonyls [J].

Angyal, Peter ;

Kotschy, Andras M. ;

Dudas, Adam ;

Varga, Szilard ;

Soos, Tibor .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (02)

[3] Copper-catalyzed formylation of alkenyl C-H bonds using BrCHCl2 as a stoichiometric formylating reagent [J].

Bao, Yan ;

Wang, Gao-Yin ;

Zhang, Ya-Xuan ;

Bian, Kang-Jie ;

Wang, Xi-Sheng .

CHEMICAL SCIENCE, 2018, 9 (11) :2986-2990

[4] The Heck coupling reaction using aryl vinyl ketones: Synthesis of flavonoids [J].

Bianco, A ;

Cavarischia, C ;

Guiso, M .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (13) :2894-2898

[5] Rhodium-Catalyzed and Zinc(II)-Triflate-Promoted Asymmetric Hydrogenation of Tetrasubstituted α,β-Unsaturated Ketones [J].

Calvin, Joel R. ;

Frederick, Michael O. ;

Laird, Dana L. T. ;

Remacle, Jacob R. ;

May, Scott A. .

ORGANIC LETTERS, 2012, 14 (04) :1038-1041

[6] Synthesis of Benzocyclobutenes by Palladium-Catalyzed C-H Activation of Methyl Groups: Method and Mechanistic Study [J].

Chaumontet, Manon ;

Piccardi, Riccardo ;

Audic, Nicolas ;

Hitce, Julien ;

Peglion, Jean-Louis ;

Clot, Eric ;

Baudoin, Olivier .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) :15157-15166

[7] Direct Dehydrogenation for the Synthesis of α,β-Unsaturated Carbonyl Compounds [J].

Chen, Hong ;

Liu, Long ;

Huang, Tianzeng ;

Chen, Jing ;

Chen, Tieqiao .

ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (16) :3332-3346

[8] Highly Stereoselective Synthesis of 2,2-Disubstituted Vinylphosphonates via Aryl to Vinyl 1,4-Palladium Migration [J].

Chen, Yan-Zhen ;

Bao, Geng-Yu ;

Zhan, Xin-Chen ;

Fu, Jian-Guo ;

Ji, Xiao-Ming ;

Zhang, Shu-Sheng ;

Feng, Chen-Guo .

CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (18) :2188-2192

[9] Enantioselective synthesis of quaternary 3,4-dihydroisoquinolinones via Heck carbonylation reactions: development and application to the synthesis of Minalrestat analogues [J].

Cheng, Cang ;

Wan, Bin ;

Zhou, Bo ;

Gu, Yichao ;

Zhang, Yanghui .

CHEMICAL SCIENCE, 2019, 10 (42) :9853-9858

[10] Anti-inflammatory activities of new succinic and maleic derivatives from the fruiting body of Antrodia camphorata [J].

Chien, Shih-Chang ;

Chen, Miaw-Ling ;

Kuo, Hsiou-Ting ;

Tsai, Yao-Ching ;

Lin, Bi-Fong ;

Kuo, Yueh-Hsiung .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2008, 56 (16) :7017-7022

← 1 2 3 4 5 6 7 8 →