Selenium-Catalyzed Trifluoromethylsulfinylation/Rearrangement of Allylic and Propargylic Alcohols: Access to Allylic and Allenic Triflones

被引：26

作者：

Zhu, Deng ^{[1
]}

Luo, Hui-Yun ^{[1
]}

Chen, Zhi-Min ^{[1
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, Shanghai 200240, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 03期

关键词：

D O I：

10.1021/acs.orglett.0c04236

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A selenium-catalyzed trifluoromethylsulfinylation/rearrangement of allylic and propargylic alcohols for synthesizing triflones was developed for the first time. Various allylic and allenic triflones were delivered in moderate to excellent yields. After numerous control experiments were performed, it was suggested that this transformation includes an unusual [+SCF3] group disproportionation process that forms [+SOCF3] that is in-situ-catalyzed by selenium, and H2O was used as an oxygen source. This reaction features mild reaction conditions and good compatibility of substrates, and it is transition-metal-free.

引用

页码：1044 / 1048

页数：5

共 57 条

[1] Sulfones: new reagents in organocatalysis [J].

Alba, Andrea-Nekane R. ;

Companyo, Xavier ;

Rios, Ramon .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (06) :2018-2033

[2] Reactions of allyl alcohols and boronic acids with trifluoromethanesulfonyl hypervalent iodonium ylide under copper-catalysis [J].

Arimori, Sadayuki ;

Takada, Masahiro ;

Shibata, Norio .

DALTON TRANSACTIONS, 2015, 44 (45) :19456-19459

[3] Synthesis, rearrangement and solvolysis of propargylic and allylic trifluoromethanesulfinates [J].

Braverman, S ;

Pechenick, T ;

Zafrani, Y .

ARKIVOC, 2004, :51-63

[4] HIGHLY REACTIVE SULFINATES - THE SYNTHESIS, SOLVOLYSIS AND REARRANGEMENT OF BENZYL TRICHLOROMETHANESULFINATES [J].

BRAVERMAN, S ;

DUAR, Y .

TETRAHEDRON, 1990, 46 (08) :2975-2990

[5] Facile synthesis and rearrangement of propargylic trifluoromethanesulfinates [J].

Braverman, S ;

Pechenick, T ;

Zafrani, Y .

TETRAHEDRON LETTERS, 2001, 42 (07) :1391-1393

[6] Regio- and Enantioselective Preparation of Chiral Allylic Sulfones Featuring Elusive Quaternary Stereocenters [J].

Cai, Aijie ;

Kleij, Arjan W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (42) :14944-14949

[7] One-Pot Synthesis of Allylic Sulfones, Ketosulfones, and Triflyl Allylic Alcohols from Domino Reactions of Allylic Alcohols with Sulfinic Acid under Metal-Free Conditions [J].

Chu, Xue-Qiang ;

Meng, Hua ;

Xu, Xiao-Ping ;

Ji, Shun-Jun .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (32) :11359-11368

[8] Catalytic, Enantioselective Sulfenylation of Ketone-Derived Enoxysilanes [J].

Denmark, Scott E. ;

Rossi, Sergio ;

Webster, Matthew P. ;

Wang, Hao .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (37) :13016-13028

[9] Lewis Base Catalyzed, Enantioselective, Intramolecular Sulfenoamination of Olefins [J].

Denmark, Scott E. ;

Chi, Hyung Min .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (25) :8915-8918

[10] Catalytic Asymmetric Thiofunctionalization of Unactivated Alkenes [J].

Denmark, Scott E. ;

Kornfilt, David J. P. ;

Vogler, Thomas .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (39) :15308-15311

← 1 2 3 4 5 6 →