Copper-Catalyzed Oxyalkynylation of C-S Bonds in Thiiranes and Thiethanes with Hypervalent Iodine Reagents

被引：34

作者：

Borrel, Julien ^{[1
]}

Pisella, Guillaume ^{[1
]}

Waser, Jerome ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne, Inst Chem Sci & Engn, Lab Catalysis & Organ Synth, SB,ISIC,LCSO,BCH 1402, CH-1015 Lausanne, Switzerland

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 02期

基金：

瑞士国家科学基金会;

关键词：

RING-OPENING REACTIONS; ALKYNYLATION; EPOXIDES; OXETANES; EPISULFIDES; DERIVATIVES; EFFICIENT; SULFIDES; INDOLE; THIOLS;

D O I：

10.1021/acs.orglett.9b04157

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the oxyalkynylation of thiiranes and thietanes using ethynylbenziodoxolone reagents (EBXs) to readily access functionalized building blocks bearing an alkynyl, a benzoate, and an iodide group. The reaction proceeds with high atom efficiency most likely through an alkynyl-episulfonium intermediate. The transformation is copper-catalyzed and compatible with a large array of thiiranes and thietanes.

引用

页码：422 / 427

页数：6

共 54 条

[1] Ring-opening reactions of oxetanes: A review of methodology development and synthetic applications [J].

Ahmad, Sajjad ;

Yousaf, Muhammad ;

Mansha, Asim ;

Rasool, Nasir ;

Zahoor, Ameer Fawad ;

Hafeez, Freeha ;

Rizvi, Sayyad Muhammad Ali .

SYNTHETIC COMMUNICATIONS, 2016, 46 (17) :1397-1416

[2] Nucleophilic ring opening reactions of aziridines [J].

Akhtar, Rabia ;

Naqvi, Syed Ali Raza ;

Zahoor, Ameer Fawad ;

Saleem, Sameera .

MOLECULAR DIVERSITY, 2018, 22 (02) :447-501

[3] A Density Functional Theory (DFT) Mechanistic Study of Gold(I)-Catalyzed Alkynylation of the Indole and Pyrrole Substrates, Using a Hypervalent Iodine Reagent [J].

Ariafard, Alireza .

ACS CATALYSIS, 2014, 4 (09) :2896-2907

[4] Atom-economical group-transfer reactions with hypervalent iodine compounds [J].

Boelke, Andreas ;

Finkbeiner, Peter ;

Nachtsheim, Boris J. .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 :1263-1280

[5] Tandem Catalytic C(sp3)-H Amination/Sila-Sonogashira-Hagihara Coupling Reactions with Iodine Reagents [J].

Buendia, Julien ;

Darses, Benjamin ;

Dauban, Philippe .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (19) :5697-5701

[6] Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry [J].

Bull, James A. ;

Croft, Rosemary A. ;

Davis, Owen A. ;

Doran, Robert ;

Morgan, Kate F. .

CHEMICAL REVIEWS, 2016, 116 (19) :12150-12233

[7] Applications of cyclic sulfates of vic-diols: Synthesis of episulfides, olefins, and thio sugars [J].

CalvoFlores, FG ;

GarciaMendoza, P ;

HernandezMateo, F ;

IsacGarcia, J ;

SantoyoGonzalez, F .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) :3944-3961

[8] Cysteinyl-leukotrienes and their receptors in asthma and other inflammatory diseases: Critical update and emerging trends [J].

Capra, Valerie ;

Thompson, Miles D. ;

Sala, Angelo ;

Cole, David E. ;

Folco, Giancarlo ;

Rovati, G. Enrico .

MEDICINAL RESEARCH REVIEWS, 2007, 27 (04) :469-527

[9]

CHAN TH, 1974, TETRAHEDRON LETT, P2091

[10]

Chew W., 1993, SULFUR REP, V15, P1, DOI [DOI 10.1080/01961779308050628, 10.1080/01961779308050628]

← 1 2 3 4 5 6 →