A stereoselective route to (E)-vinylic selenides through the palladium-catalyzed cross-coupling reaction of selenovinylicdialkylboranes with alkyl halides

被引:11
作者
Yang, Y [1 ]
Huang, X [1 ]
机构
[1] HANGZHOU UNIV,DEPT CHEM,HANGZHOU 310028,PEOPLES R CHINA
基金
中国国家自然科学基金;
关键词
D O I
10.1080/00397919708005038
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of selenoviylicdialkyboranes with alkyl halides takes place readily in the presence of Pd(PPh(3))(4) and sodium methoxide to afford (E)-vinylic selenides in excellent yields.
引用
收藏
页码:345 / 349
页数:5
相关论文
共 9 条
[1]   VICINAL DIFUNCTIONALIZATION OF ALKYNYL SELENIDES WITH LITHIUM BUTYLCYANOCUPRATE AND ELECTROPHILES [J].
BRAGA, AL ;
RECKZIEGEL, A ;
SILVEIRA, CC ;
COMASSETO, JV .
SYNTHETIC COMMUNICATIONS, 1994, 24 (08) :1165-1170
[2]   HYDROBORATION .36. DIRECT ROUTE TO 9-BORABICYCLO[3.3.1]NONANE VIA CYCLIC HYDROBORATION OF 1,5-CYCLOOCTADIENE - 9-BORABICYCLO[3.3.1]NONANE AS A UNIQUELY SELECTIVE REAGENT FOR HYDROBORATION OF OLEFINS [J].
BROWN, HC ;
KNIGHTS, EF ;
SCOUTEN, CG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (25) :7765-7770
[3]   ADDITION COMPOUNDS OF THE ALKALI METAL HYDRIDES .9. THE REACTION OF LEWIS ACIDS OF BORON WITH SODIUM HYDRIDE AND BOROHYDRIDE [J].
BROWN, HC ;
TIERNEY, PA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (07) :1552-1558
[4]  
BROWN HC, 1971, J AM CHEM SOC, V93, P1817
[5]  
COULSON DR, 1972, INORG SYNTH, V13, P569
[6]   A STEREOSELECTIVE ROUTE TO ALKENYL SULFIDES THROUGH THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF 9-ALKYL-9-BBN WITH 1-BROMO-1-PHENYLTHIOETHENE OR (E)-2-BROMO-1-PHENYLTHIO-1-ALKENES AND (Z)-2-BROMO-1-PHENYLTHIO-1-ALKENES [J].
HOSHINO, Y ;
ISHIYAMA, T ;
MIYAURA, N ;
SUZUKI, A .
TETRAHEDRON LETTERS, 1988, 29 (32) :3983-3986
[7]   STEREOSELECTIVE SYNTHESES OF CONJUGATED 1-PHENYLTHIO-1,3-ALKADIENES AND 1,3,5-ALKATRIENES THROUGH THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF (E)- OR (Z)-1-ALKENYLBORONATES WITH (E)- OR (Z)-2-BROMO-1-PHENYLTHIO-1-ALKENES [J].
ISHIYAMA, T ;
MIYAURA, N ;
SUZUKI, A .
CHEMISTRY LETTERS, 1987, (01) :25-28
[8]   PALLADIUM-CATALYZED CROSS-COUPLING OF (2-ETHOXYVINYL)BORANES WITH ARYL AND BENZYL HALIDES - A NEW METHOD FOR CONVERSION OF ORGANIC HALIDES INTO ALDEHYDES WITH 2 MORE CARBON-ATOMS [J].
MIYAURA, N ;
MAEDA, K ;
SUGINOME, H ;
SUZUKI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (11) :2117-2120
[9]   ORGANOSELENIUM CHEMISTRY .6. STEREOSELECTIVE SYNTHESIS OF (E)-1-PHENYLSELENO-1-ALKENES AND (Z)-1-(PHENYLSELENO)-1-ALKENES [J].
RAUCHER, S ;
HANSEN, MR ;
COLTER, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (25) :4885-4887