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2016 Fiscal Year Final Research Report

Development of organosilicon reagents that react without recourse to activators

Research Project

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Project/Area Number 26620081
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionKyoto University

Principal Investigator

Yorimitsu Hideki  京都大学, 理学研究科, 教授 (00372566)

Research Collaborator YAMAMOTO Yutaro  京都大学, 大学院理学研究科, 大学院生
OTSUKA Shinya  京都大学, 大学院理学研究科, 大学院生
NOGI Keisuke  京都大学, 大学院理学研究科, 助教
OSUKA Atsuhiro  京都大学, 大学院理学研究科, 教授
MATSUBARA Hiroshi  大阪府立大学, 大学院理学研究科, 教授
Project Period (FY) 2014-04-01 – 2017-03-31
Keywordsトランスメタル化 / クロスカップリング / パラジウム / ケイ素 / ホウ素 / 塩化アリール
Outline of Final Research Achievements

Palladium-catalyzed silylation of aryl chlorides with silylsilatranes proceeds under activator-free conditions, hence displaying wide functional group compatibility to allow boryl and siloxy groups to survive. Experimental and computational studies have revealed that smooth transmetalation from silylsilatranes to arylpalladium chloride is facilitated by strong interaction between the Lewis acidic silicon and the chloride.
Similarly, bis(pinacolato)diboron and pinacolatoborane underwent activator-free borylation and reduction of aryl chlorides, respectively, which again takes advantage of strong interaction between the Lewis acidic boron and the chloride.
The cross-coupling reactions of arylsilatranes with aryl chlorides required tetrabutylammonium fluoride as an activator for smooth transmetalation.

Free Research Field

有機化学

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Published: 2018-03-22  

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