Metal-Free Transfer Hydroiodination of C-C Multiple Bonds

被引：39

作者：

Chen, Weiqiang ^{[1
]}

Walker, Johannes C. L. ^{[1
]}

Oestreich, Martin ^{[1
]}

机构：

[1] Tech Univ Berlin, Inst Chem, Str 17 Juni 115, D-10623 Berlin, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 02期

关键词：

STEREOSPECIFIC HYDROHALOGENATION REACTION; HIGHLY STEREOSELECTIVE-SYNTHESIS; SURFACE-MEDIATED REACTIONS; B(C6F5)(3)-CATALYZED TRANSFER; UNSATURATED-HYDROCARBONS; TERMINAL ALKYNES; CONVENIENT; ALKENES; EFFICIENT; ACID;

D O I：

10.1021/jacs.8b12318

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The design and a gram-scale synthesis of a bench-stable cyclohexa-1,4-diene-based surrogate of gaseous hydrogen iodide are described. By initiation with a moderately strong Bronsted acid, hydrogen iodide is transferred from the surrogate onto C-C multiple bonds such as alkynes and allenes without the involvement of free hydrogen iodide. The surrogate fragments into toluene and ethylene, easy-to-remove volatile waste. This hydroiodination reaction avoids precarious handling of hydrogen iodide or hydroiodic acid. By this, a broad range of previously unknown or difficult-to-prepare vinyl iodides can be accessed in stereocontrolled fashion.

引用

页码：1135 / 1140

页数：6

共 59 条

[1] A convergent approach to (R)-Tiagabine by a regio- and stereocontrolled hydroiodination of alkynes [J].

Bartoli, Giuseppe ;

Cipolletti, Roberto ;

Di Antonio, Giustino ;

Giovannini, Riccardo ;

Lanari, Silvia ;

Marcolini, Mauro ;

Marcantoni, Enrico .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (15) :3509-3517

[2] Shuttle Catalysis-New Strategies in Organic Synthesis [J].

Bhawal, Benjamin N. ;

Morandi, Bill .

CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (50) :12004-12013

[3] Catalytic Transfer Functionalization through Shuttle Catalysis [J].

Bhawal, Benjamin N. ;

Morandi, Bill .

ACS CATALYSIS, 2016, 6 (11) :7528-7535

[4] [(3,5-(CF3)2C6H3)4B]-[H(OET2)2]+ - A CONVENIENT REAGENT FOR GENERATION AND STABILIZATION OF CATIONIC, HIGHLY ELECTROPHILIC ORGANOMETALLIC COMPLEXES [J].

BROOKHART, M ;

GRANT, B ;

VOLPE, AF .

ORGANOMETALLICS, 1992, 11 (11) :3920-3922

[5] A simple and versatile method for the hydroiodination of alkenes and alkynes using I2 and Et3SiH in the presence of copper(II) [J].

Campos, PJ ;

García, B ;

Rodríguez, MA .

TETRAHEDRON LETTERS, 2002, 43 (35) :6111-6112

[6] Bronsted Acid-Catalyzed Transfer Hydrogenation of Imines and Alkenes Using Cyclohexa-1,4-dienes as Dihydrogen Surrogates [J].

Chatterjee, Indranil ;

Oestreich, Martin .

ORGANIC LETTERS, 2016, 18 (10) :2463-2466

[7] B(C6F5)3-Catalyzed Transfer of Dihydrogen from One Unsaturated Hydrocarbon to Another [J].

Chatterjee, Indranil ;

Qu, Zheng-Wang ;

Grimme, Stefan ;

Oestreich, Martin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (41) :12158-12162

[8] Copper-Catalyzed trans-Carbohalogenation of Terminal Alkynes with Functionalized Tertiary Alkyl Halides [J].

Che, Chao ;

Zheng, Hanliang ;

Zhu, Gangguo .

ORGANIC LETTERS, 2015, 17 (06) :1617-1620

[9] Poly[styrene(iodosodiacetate)]-promoted ring expansion reaction of 1-alky-nylcycloalkanols:: A novel synthesis of (Z)-2-(1-iodo-1-organyl)methylene-cycloalkanones [J].

Chen, JM ;

Huang, X .

SYNTHESIS-STUTTGART, 2004, (15) :2459-2462

[10] Convenient, in situ generation of anhydrous hydrogen iodide for the preparation of α-glycosyl iodides and vicinal iodohydrins and for the catalysis of Ferrier glycosylation [J].

Chervin, SM ;

Abada, P ;

Koreeda, M .

ORGANIC LETTERS, 2000, 2 (03) :369-372

← 1 2 3 4 5 6 →