The chemistry of borylstannanes: Oxidative addition to palladium species and its application to palladium-catalyzed borylstannation of alkynes

被引:119
作者
Onozawa, S [1 ]
Hatanaka, Y [1 ]
Sakakura, T [1 ]
Shimada, S [1 ]
Tanaka, M [1 ]
机构
[1] NATL INST MAT & CHEM RES,TSUKUBA,IBARAKI 305,JAPAN
关键词
D O I
10.1021/om9607199
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
cis addition of the borylstannanes Me(3)SnB[NMe(CH2CH2)NMe] (1) and Me(3)SnB(NEt(2))(2) (4) across alkynes was efficiently catalyzed at room temperature or 80 degrees C by Pd(PPh(3))(4), Pd(dba)(2), Cl2Pd(PPh(3))(2), or Me(2)Pd[PMe(2)(CH2CH2)PMe(2)] to give (beta-stannylalkenyl)boranes in high yields. Treatments of 1 with Me(2)Pd[PMe(2)(CH2CH2)PMe(2)] and of 4 with cis-Me(2)Pd(PPh(2)Me)(2) gave [{MeN(CH2CH2)Men}B](Me(3)Sn)Pd[PMe(2) (CH2CH2)-PMe(2)] (5) and [(Et(2)N)(2)B](Me(3)Sn)Pd(PPh(2)Me)(2) (6), respectively, with the former characterized by X-ray analysis. Complex 5, when treated with 1-octyne, formed the corresponding (beta-stannyl-1-octen-1-yl)borane and could catalyze the addition reaction of 1 with 1-octyne.
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页码:5450 / 5452
页数:3
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