Palladium-Catalyzed Regio- and Stereoselective Hydrosilylation of Electron-Deficient Alkynes

被引:68
作者
Sumida, Yuto [1 ]
Kato, Tomoe [1 ]
Yoshida, Suguru [1 ]
Hosoya, Takamitsu [1 ]
机构
[1] Tokyo Med & Dent Univ, Biol Chem Lab, Grad Sch Biomed Sci, Inst Biomat & Bioengn,Chiyoda Ku, Tokyo 1010062, Japan
关键词
HYDROSTANNATION; EFFICIENT; (Z)-ALKENYLSILANES; HYDROSILATION; COMPLEXES; SILICON; OLEFINS; KETONES;
D O I
10.1021/ol300279c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Highly regio- and stereoselective hydrosilylation applicable to a broad range of electron-deficient alkynes has been established using palladium catalysis. The synthetic utility of the method has been demonstrated by further transformations of alpha-silylalkenes, particularly Hiyama coupling and stereoinverting iododesilylation followed by Suzuki-Miyaura coupling, which enables stereodivergent syntheses of alpha-arylenoates.
引用
收藏
页码:1552 / 1555
页数:4
相关论文
共 30 条
[1]   Synthesis of α-iodo-α,β-unsaturated ketones by the reaction of α-silyl-α,β-unsaturated ketones with ICl or ICl-AlCl3 [J].
Alimardanov, A ;
Negishi, E .
TETRAHEDRON LETTERS, 1999, 40 (20) :3839-3842
[2]  
[Anonymous], 1992, COMPREHENSIVE HDB HY, DOI DOI 10.1016/C2009-0-11185-6
[3]  
Brook M. A., 2000, SILICON ORGANIC ORGA
[4]   MECHANISTIC ASPECTS OF THE PLATINUM CATALYZED HYDROSILYLATION OF PHCH=CH2 WITH ET3SIH [J].
CASERI, W ;
PREGOSIN, PS .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 356 (02) :259-269
[5]   HOMOGENEOUS CATALYSIS .2. MECHANISM OF HYDROSILATION OF OLEFINS CATALYZED BY GROUP 8 METAL COMPLEXES [J].
CHALK, AJ ;
HARROD, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (01) :16-&
[6]   PALLADIUM(O) CATALYSIS IN HYDROSTANNATION OF CARBON-CARBON TRIPLE BONDS [J].
COCHRAN, JC ;
BRONK, BS ;
TERRENCE, KM ;
PHILLIPS, HK .
TETRAHEDRON LETTERS, 1990, 31 (46) :6621-6624
[7]  
Denmark S. E., 2004, METAL CATALYZED CROS
[8]   Stereoselective synthesis of stannyl enones via palladium-catalyzed and free radical hydrostannation of alkynyl ketones with trineophyltin hydride [J].
Dodero, VI ;
Koll, LC ;
Faraoni, MB ;
Mitchell, TN ;
Podestá, JC .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (26) :10087-10091
[9]   DICOBALT OCTACARBONYL AS A CATALYST FOR HYDROSILATION OF OLEFINS [J].
HARROD, JF ;
CHALK, AJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (05) :1133-&
[10]   Asymmetric hydrosilylation of styrenes catalyzed by palladium-MOP complexes: Ligand modification and mechanistic studies [J].
Hayashi, T ;
Hirate, S ;
Kitayama, K ;
Tsuji, H ;
Torii, A ;
Uozumi, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) :1441-1449