A zwitterionic carbanion frustrated by boranes - Dihydrogen cleavage with weak lewis acids via an "inverse" frustrated lewis pair approach

Hui Li; Adelia J.A. Aquino; David B. Cordes; Fernando Hung-Low; William L. Hase; Clemens Krempner

doi:10.1021/ja409330h

A zwitterionic carbanion frustrated by boranes - Dihydrogen cleavage with weak lewis acids via an "inverse" frustrated lewis pair approach

Hui Li, Adelia J.A. Aquino, David B. Cordes, Fernando Hung-Low, William L. Hase, Clemens Krempner

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

58 Scopus citations

Abstract

The synthesis, structural characterization, and acid-base chemistry of [C(SiMe₂OCH₂CH₂OMe)₃]Na (2), a sterically encumbered zwitterionic organosodium compound, is reported. 2 is a strong Brønsted base that forms frustrated Lewis pairs (FLPs) with a number of boron-containing Lewis acids ranging from weakly Lewis acidic aryl and alkyl boranes to various alkyl borates. These intermolecular FLPs readily cleave H₂, which confirms that even poor Lewis acids can engage in FLP-mediated H₂ cleavage provided that the present bulky base is of sufficiently high Brønsted basicity.

Original language	English
Pages (from-to)	16066-16069
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	135
Issue number	43
DOIs	https://doi.org/10.1021/ja409330h
State	Published - Oct 30 2013

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abstract = "The synthesis, structural characterization, and acid-base chemistry of [C(SiMe2OCH2CH2OMe)3]Na (2), a sterically encumbered zwitterionic organosodium compound, is reported. 2 is a strong Br{\o}nsted base that forms frustrated Lewis pairs (FLPs) with a number of boron-containing Lewis acids ranging from weakly Lewis acidic aryl and alkyl boranes to various alkyl borates. These intermolecular FLPs readily cleave H2, which confirms that even poor Lewis acids can engage in FLP-mediated H2 cleavage provided that the present bulky base is of sufficiently high Br{\o}nsted basicity.",

author = "Hui Li and Aquino, {Adelia J.A.} and Cordes, {David B.} and Fernando Hung-Low and Hase, {William L.} and Clemens Krempner",

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T1 - A zwitterionic carbanion frustrated by boranes - Dihydrogen cleavage with weak lewis acids via an "inverse" frustrated lewis pair approach

AU - Li, Hui

AU - Aquino, Adelia J.A.

AU - Cordes, David B.

AU - Hung-Low, Fernando

AU - Hase, William L.

AU - Krempner, Clemens

PY - 2013/10/30

Y1 - 2013/10/30

N2 - The synthesis, structural characterization, and acid-base chemistry of [C(SiMe2OCH2CH2OMe)3]Na (2), a sterically encumbered zwitterionic organosodium compound, is reported. 2 is a strong Brønsted base that forms frustrated Lewis pairs (FLPs) with a number of boron-containing Lewis acids ranging from weakly Lewis acidic aryl and alkyl boranes to various alkyl borates. These intermolecular FLPs readily cleave H2, which confirms that even poor Lewis acids can engage in FLP-mediated H2 cleavage provided that the present bulky base is of sufficiently high Brønsted basicity.

AB - The synthesis, structural characterization, and acid-base chemistry of [C(SiMe2OCH2CH2OMe)3]Na (2), a sterically encumbered zwitterionic organosodium compound, is reported. 2 is a strong Brønsted base that forms frustrated Lewis pairs (FLPs) with a number of boron-containing Lewis acids ranging from weakly Lewis acidic aryl and alkyl boranes to various alkyl borates. These intermolecular FLPs readily cleave H2, which confirms that even poor Lewis acids can engage in FLP-mediated H2 cleavage provided that the present bulky base is of sufficiently high Brønsted basicity.

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A zwitterionic carbanion frustrated by boranes - Dihydrogen cleavage with weak lewis acids via an "inverse" frustrated lewis pair approach

Abstract

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