Trialkylphosphonium oxoborates as C(sp3)–H oxyanion holes and their application in catalytic chemoselective acetalization

文献情報

出版日 2023-10-20

DOI 10.1039/D3SC03081D

インパクトファクター 9.825

著者

Vincent Ming-Yau Leung, Hong-Chai Fabio Wong, Chun-Man Pook, Ying-Lung Steve Tse, Ying-Yeung Yeung

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要旨

The use of trialkylphosphonium oxoborates (TOB) as catalysts is reported. The site-isolated borate counter anion in a TOB catalyst increases the availability of C(sp3)–H to interact with electron donor substrates. The catalytic protocol is applicable to a wide range of substrates in the acetalization reaction and provides excellent chemoselectivity in the acetalization over thioacetalization in the presence of alcohols and thiols, which is otherwise hard to achieve using typical acid catalysts. Experimental and computational studies revealed that the TOB catalysts have multiple preorganized C(sp3)–Hs that serve as a mimic of oxyanion holes, which can stabilize the oxyanion intermediates via multiple C(sp3)–H non-classical hydrogen bond interactions.

掲載誌

Chemical Science

CiteScore: 14.4

自己引用率: 3.9%

年間論文数: 1413

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Trialkylphosphonium oxoborates as C(sp3)–H oxyanion holes and their application in catalytic chemoselective acetalization

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