Highly Selective Hydroiodation of Alkynes Using an Iodine-Hydrophosphine Binary System

被引:55
作者
Kawaguchi, Shin-ichi [1 ]
Ogawa, Akiya [1 ]
机构
[1] Osaka Prefecture Univ, Dept Appl Chem, Grad Sch Engn, Naka Ku, Osaka 5998531, Japan
基金
日本学术振兴会;
关键词
ALKENES; ALCOHOLS; IODIDES; HYDROIODINATION; IODINATION; GENERATION; HALIDES; KETONES; ESTERS; I-2;
D O I
10.1021/ol1005246
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel hydroiodation of alkynes (1) using an iodine/hydrophosphine binary system takes place regioselectively to provide the corresponding Markovnikov-type adducts (2) in good yield. This hydroiodation is advantageous in terms of mild conditions, convenient operation, and tolerance to various functional groups.
引用
收藏
页码:1893 / 1895
页数:3
相关论文
共 28 条
[1]   New approach to phosphinoalkynes based on Pd- and Ni-catalyzed cross-coupling of terminal alkynes with chlorophosphanes [J].
Beletskaya, IP ;
Afanasiev, VV ;
Kazankova, MA ;
Efimova, IV .
ORGANIC LETTERS, 2003, 5 (23) :4309-4311
[2]   HYDROBORATION .69. HYDROBORATION CHARACTERISTICS OF LITHIUM BOROHYDRIDE ETHYL-ACETATE IN ETHYL ETHER - A NEW SYSTEM FOR CONTROLLED HYDROBORATION OF ALKENES AND ALKYNES [J].
BROWN, HC ;
SOMAYAJI, V ;
NARASIMHAN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (25) :4822-4827
[3]   VINYLIC ORGANOBORANES .13. A CONVENIENT STEREOSPECIFIC SYNTHESIS OF (Z)-1-HALO-1-ALKENES FROM 1-ALKYNES VIA (E)-1-ALKENYLBORANE DERIVATIVES WITH HALOGENS [J].
BROWN, HC ;
SUBRAHMANYAM, C ;
HAMAOKA, T ;
RAVINDRAN, N ;
BOWMAN, DH ;
MISUMI, S ;
UNNI, MK ;
SOMAYAJI, V ;
BHAT, NG .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) :6068-6075
[4]   STEREOCHEMISTRY OF ADDITION-REACTIONS OF ALLENES .6. ORIENTATION AND STEREOCHEMISTRY OF RADICAL-ADDITION [J].
BYRD, LR ;
CASERIO, MC .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (24) :3881-&
[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]   Practical procedures for the preparation of N-tert-butyldimethylsilylhydrazones and their use in modified Wolff-Kishner reductions and in the synthesis of vinyl halides and gem-dihalides [J].
Furrow, ME ;
Myers, AG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (17) :5436-5445
[7]   STEREOSELECTIVE AND REGIOSELECTIVE GENERATION OF ALKENYLZINC REAGENTS VIA TITANIUM-CATALYZED HYDROZINCATION OF INTERNAL ACETYLENES [J].
GAO, Y ;
HARADA, K ;
HATA, T ;
URABE, H ;
SATO, F .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (02) :290-291
[8]  
GOMELYA ND, 1987, ZH OBSHCH KHIM+, V57, P1702
[9]  
GOMELYA ND, 1988, ZH OBSHCH KHIM+, V58, P2652
[10]  
GOMELYA ND, 1984, ZH OBSHCH KHIM+, V54, P1242