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Hydroboration of alkynylchlorosilanes as an efficient route for the synthesis of SiNNB heterocycles
Applied Organometallic Chemistry ( IF 3.9 ) Pub Date : 2021-09-07 , DOI: 10.1002/aoc.6447
Ezzat Khan 1, 2
Affiliation  

Alkenylsilanes bearing chlorosilyl and boryl groups geminally attached to a carbon atom ((E)-3-(9-borabicyclo[3.3.1]nonan-9-yl)-N,N-dimethyl-3-(trichlorosilyl)prop-2-en-1-amine, 1, (1-(9-borabicyclo[3.3.1]nonan-9-yl)-3,3-dimethylbut-1-en-1-yl)dichloro (phenyl)silane, 2, (1-(9-borabicyclo[3.3.1]nonan-9-yl)-2-phenylvinyl) chloro (methyl)(phenyl)silane, 3, (1-(9-borabicyclo[3.3.1]nonan-9-yl)hex-1-en-1-yl)trichlorosilane, 4) are accessible by hydroboration of the corresponding alkynylsilanes. Only the vinyl group of 1 adopted E configuration, which may be favored by ring closure via an intramolecular B–N bonding interaction. Compounds 24 reacted with N-trimethylsilylpyrazole and N-2-(trimethylsilylamino)pyridine by elimination of ClSiMe3 and formation of Si–N bonds. Intramolecular donor–acceptor interactions between the N and B atoms afforded five- and six-membered heterocycles, which contained Si, N, and B as heteroatoms. A bis(pyrazolyl)silane was isolated upon treatment of a dichlorosilane with two equivalents of trimethylsilylpyrazole.

中文翻译:

炔基氯硅烷的硼氢化反应是合成 SiNNB 杂环的有效途径

带有氯甲硅烷基和硼基的链烯基硅烷与碳原子 (( E )-3-(9-硼双环 [3.3.1]nonan-9-yl) -N , N-二甲基-3-(三氯甲硅烷基)prop-2- en-1-胺,1,(1-(9-硼双环[3.3.1]壬烷-9-基)-3,3-二甲基丁-1-烯-1-基)二氯(苯基)硅烷,2,( 1-(9-硼双环[3.3.1]壬烷-9-基)-2-苯基乙烯基)氯(甲基)(苯基)硅烷,3,(1-(9-硼双环[3.3.1]壬烷-9-基) )己-1-烯-1-基)三氯硅烷,4 )可通过相应炔基硅烷的硼氢化反应获得。只有1的乙烯基采用E构型,这可能有利于通过分子内 B-N 键相互作用的闭环。化合物2 - 4与反应Ñ -trimethylsilylpyrazole和Ñ通过ClSiMe消除-2-(三甲基甲硅烷基)吡啶3和形成Si-N键。N 和 B 原子之间的分子内供体-受体相互作用提供了五元和六元杂环,其中包含 Si、N 和 B 作为杂原子。在用两当量的三甲基甲硅烷基吡唑处理二氯硅烷后分离出双(吡唑基)硅烷。
更新日期:2021-09-07
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