Hydroalkylation of Alkenes Using Alkyl Iodides and Hantzsch Ester under Palladium/Light System

被引：31

作者：

Sumino, Shuhei ^{[1
]}

Ryu, Ilhyong ^{[1
]}

机构：

[1] Osaka Prefecture Univ, Grad Sch Sci, Dept Chem, Sakai, Osaka 5998531, Japan

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 01期

基金：

日本学术振兴会;

关键词：

RADICAL CONJUGATE ADDITIONS; ELECTRON-DEFICIENT ALKENES; UNACTIVATED ALKYL; ARYLBORONIC ACIDS; COUPLING REACTION; VISIBLE-LIGHT; HECK REACTION; HALIDES; CARBONYLATION; DERIVATIVES;

D O I：

10.1021/acs.orglett.5b03238

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hydroalkylation of alkenes using alkyl iodides with Hantzsch ester as a hydrogen source occurred smoothly under a Pd/light system, in a novel, tin-free Giese reaction. A chemoselective reaction at C(sp(3))-I in the presence of a C(sp(2))-X (X = Br or I) bond was attained, which allowed for the stepwise functionalization of two types of C-X bonds in a one-pot procedure.

引用

页码：52 / 55

页数：4

共 40 条

[1] Investigating the Rate of Photoreductive Glucosyl Radical Generation [J].

Andrews, R. Stephen ;

Becker, Jennifer J. ;

Gagne, Michel R. .

ORGANIC LETTERS, 2011, 13 (09) :2406-2409

[2] Intermolecular Addition of Glycosyl Halides to Alkenes Mediated by Visible Light [J].

Andrews, R. Stephen ;

Becker, Jennifer J. ;

Gagne, Michel R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) :7274-7276

[3] Palladium-Catalyzed Heck-Type Reactions of Alkyl Iodides [J].

Bloome, Kayla S. ;

McMahen, Rebecca L. ;

Alexanian, Erik J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (50) :20146-20148

[4] A RADICAL CLOCK INVESTIGATION OF MICROSOMAL CYTOCHROME-P-450 HYDROXYLATION OF HYDROCARBONS - RATE OF OXYGEN REBOUND [J].

BOWRY, VW ;

INGOLD, KU .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (15) :5699-5707

[5] FREE-RADICALS IN SYNTHESIS .1. A 2-STEP CARBOLACTONIZATION PROCEDURE [J].

BURKE, SD ;

FOBARE, WF ;

ARMISTEAD, DM .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (17) :3348-3350

[6] STUDIES ON FLUOROALKYLATION AND FLUOROALKOXYLATION .28. PALLADIUM(O)-INDUCED ADDITION OF FLUOROALKYL IODIDES TO ALKENES - AN ELECTRON-TRANSFER PROCESS [J].

CHEN, QY ;

YANG, ZY ;

ZHAO, CX ;

QIU, ZM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (03) :563-567

[7] EVIDENCE THAT PALLADIUM(0)-PROMOTED CYCLIZATIONS OF UNSATURATED ALPHA-IODOCARBONYLS OCCUR BY AN ATOM TRANSFER MECHANISM [J].

CURRAN, DP ;

CHANG, CT .

TETRAHEDRON LETTERS, 1990, 31 (07) :933-936

[8] Fluorous tin hydrides: A new family of reagents for use and reuse in radical reactions [J].

Curran, DP ;

Hadida, S ;

Kim, SY ;

Luo, ZY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (28) :6607-6615

[9] Flow Giese reaction using cyanoborohydride as a radical mediator [J].

Fukuyama, Takahide ;

Kawamoto, Takuji ;

Kobayashi, Mikako ;

Ryu, Ilhyong .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 :1791-1796

[10] Pd/Light-Accelerated Atom-Transfer Carbonylation of Alkyl Iodides: Applications in Multicomponent Coupling Processes Leading to Functionalized Carboxylic Acid Derivatives [J].

Fusano, Akira ;

Sumino, Shuhei ;

Nishitani, Satoshi ;

Inouye, Takaya ;

Morimoto, Keisuke ;

Fukuyama, Takahide ;

Ryu, Ilhyong .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (30) :9415-9422

← 1 2 3 4 →