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Transition-Metal-Free Boryl Substitution Using Silylboranes and Alkoxy Bases

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Title: Transition-Metal-Free Boryl Substitution Using Silylboranes and Alkoxy Bases
Authors: Yamamoto, Eiji Browse this author
Maeda, Satoshi Browse this author
Taketsugu, Tetsuya Browse this author
Ito, Hajime Browse this author →KAKEN DB
Keywords: silylborane
boryl substitution
halogenophilic attack
Issue Date: Jul-2017
Publisher: Georg Thieme Verlag
Journal Title: Synlett
Volume: 28
Issue: 11
Start Page: 1258
End Page: 1267
Publisher DOI: 10.1055/s-0036-1588772
Abstract: Silylboranes are used as borylation reagents for organohalides in the presence of alkoxy bases without transition-metal catalysts. PhMe2Si-B(pin) reacts with a variety of aryl, alkenyl, and alkyl halides, including sterically hindered examples, to provide the corresponding organoboronates in good yields with high borylation/silylation ratios, showing good functional group compatibility. Halogenophilic attack of a silyl nucleophile on organohalides, and subsequent nucleophilic attack on the boron electrophile are identified to be crucial, based on the results of extensive theoretical and experimental studies. This borylation reaction is further applied to the first direct dimesitylboryl (BMes(2)) substitution of aryl halides using Ph2MeSi-BMes(2) and Na(O-t-Bu), affording aryldimesitylboranes, which are regarded as an important class of compounds for organic materials. 1 Introduction 2 Boryl Substitution of Organohalides with PhMe2Si-B(pin)/Alkoxy Bases 3 Mechanistic Investigations 4 DFT Mechanistic Studies Using an Artificial Force Induced Reaction (AFIR) Method 5 Dimesitylboryl Substitution of Aryl Halides with Ph2MeSi-BMes(2)/Na(O-t-Bu) 6 Conclusion
Type: article (author version)
Appears in Collections:工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 伊藤 肇

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