Photoredox-Catalyzed Alkenylation of Benzylsulfonium Salts

被引：37

作者：

Otsuka, Shinya ^{[1
,2
]}

Nogi, Keisuke ^{[1
]}

Rovis, Tomislav ^{[2
]}

Yorimitsu, Hideki ^{[1
]}

机构：

[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan

[2] Columbia Univ, Dept Chem, 3000 Broadway, New York, NY 10027 USA

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2019年 / 14卷 / 04期

关键词：

alkenylation; photoredox catalysis; radical reaction; sulfonium; HECK-TYPE ALKENYLATION; S BOND-CLEAVAGE; DIASTEREOSELECTIVE SYNTHESIS; ELECTROCHEMICAL REDUCTION; SULFONIUM SALTS; STEREOSELECTIVE-SYNTHESIS; RADICAL ALKENYLATION; LIGHT; ARYL; ALKENES;

D O I：

10.1002/asia.201801732

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Visible light-mediated radical alkenylation of benzylsulfonium salts was achieved by means of fac-Ir(ppy)(3) as a photocatalyst, giving allylbenzenes as products. A variety of functional groups, such as halogen, ester, and cyano, were well tolerated in this transformation. Starting benzylsulfonium salts could be readily prepared from benzyl alcohols by an acid-mediated substitution, increasing the synthetic utility of this transformation.

引用

页码：532 / 536

页数：5

共 71 条

[1]

Acton A.Q., 2012, ADV RES APPL

[2] ELECTROLYTIC REDUCTIVE COUPLING .13. INTRAMOLECULAR REDUCTIVE COUPLING . ELECTROHYDROCYCLIZATION [J].

ANDERSON, JD ;

BAIZER, MM ;

PETROVIC.JP .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (12) :3890-+

[3]

[Anonymous], METAL CATALYZED CROS

[4]

[Anonymous], ANGEW CHEM

[5]

[Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1135/CCCC2011078

[6] Trifluoromethylation of aromatic alkenes by visible-light-driven photoredox catalysis: Direct conversion of alkenes to 3-trifluoromethyl-1-propenyl and 1,3-bis(trifluoromethyl)-1-propenyl derivatives [J].

Asano, Masashi ;

Tomita, Ren ;

Koike, Takashi ;

Akita, Munetaka .

JOURNAL OF FLUORINE CHEMISTRY, 2015, 179 :83-88

[7]

BEAK P, 1982, J AM CHEM SOC, V104, P4450, DOI 10.1021/ja00380a020

[8] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

[9]

Beller M., 2004, Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals

[10] THE PREPARATION AND PROPERTIES OF TRIPHENYLSULFONIUM POLYHALIDES [J].

BONNER, WA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (20) :5078-5082

← 1 2 3 4 5 6 7 8 →