An Aluminum Hydride That Functions like a Transition-Metal Catalyst

Zhi Yang; Mingdong Zhong; Xiaoli Ma; Susmita De; Chakkittakandiyil Anusha; Pattiyil Parameswaran; Herbert W. Roesky

doi:10.1002/anie.201503304

An Aluminum Hydride That Functions like a Transition-Metal Catalyst

Zhi Yang^*, Mingdong Zhong, Xiaoli Ma, Susmita De, Chakkittakandiyil Anusha, Pattiyil Parameswaran, Herbert W. Roesky

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

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

200 Citations (Scopus)

Abstract

The reaction of [LAlH₂] (L=HC(CMeNAr)₂, Ar=2,6-iPr₂C₆H₃) with MeOTf (Tf=SO₂CF₃) resulted in the formation of [LAlH(OTf)] (1) in high yield. The triflate substituent in 1 increases the positive charge at the aluminum center, which implies that 1 has a strong Lewis acidic character. The excellent catalytic activity of 1 for the hydroboration of organic compounds with carbonyl groups was investigated. Furthermore, it was shown that 1 effectively initiates the addition reaction of trimethylsilyl cyanide (TMSCN) to both aldehydes and ketones. Quantum mechanical calculations were carried out to explore the reaction mechanism.

Original language	English
Pages (from-to)	10225-10229
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	35
DOIs	https://doi.org/10.1002/anie.201503304
Publication status	Published - 1 Aug 2015

Keywords

aluminum
homogeneous catalysis
hydrides
hydroboration
hydrosilylation

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title = "An Aluminum Hydride That Functions like a Transition-Metal Catalyst",

abstract = "The reaction of [LAlH2] (L=HC(CMeNAr)2, Ar=2,6-iPr2C6H3) with MeOTf (Tf=SO2CF3) resulted in the formation of [LAlH(OTf)] (1) in high yield. The triflate substituent in 1 increases the positive charge at the aluminum center, which implies that 1 has a strong Lewis acidic character. The excellent catalytic activity of 1 for the hydroboration of organic compounds with carbonyl groups was investigated. Furthermore, it was shown that 1 effectively initiates the addition reaction of trimethylsilyl cyanide (TMSCN) to both aldehydes and ketones. Quantum mechanical calculations were carried out to explore the reaction mechanism.",

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T1 - An Aluminum Hydride That Functions like a Transition-Metal Catalyst

AU - Yang, Zhi

AU - Zhong, Mingdong

AU - Ma, Xiaoli

AU - De, Susmita

AU - Anusha, Chakkittakandiyil

AU - Parameswaran, Pattiyil

AU - Roesky, Herbert W.

PY - 2015/8/1

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N2 - The reaction of [LAlH2] (L=HC(CMeNAr)2, Ar=2,6-iPr2C6H3) with MeOTf (Tf=SO2CF3) resulted in the formation of [LAlH(OTf)] (1) in high yield. The triflate substituent in 1 increases the positive charge at the aluminum center, which implies that 1 has a strong Lewis acidic character. The excellent catalytic activity of 1 for the hydroboration of organic compounds with carbonyl groups was investigated. Furthermore, it was shown that 1 effectively initiates the addition reaction of trimethylsilyl cyanide (TMSCN) to both aldehydes and ketones. Quantum mechanical calculations were carried out to explore the reaction mechanism.

AB - The reaction of [LAlH2] (L=HC(CMeNAr)2, Ar=2,6-iPr2C6H3) with MeOTf (Tf=SO2CF3) resulted in the formation of [LAlH(OTf)] (1) in high yield. The triflate substituent in 1 increases the positive charge at the aluminum center, which implies that 1 has a strong Lewis acidic character. The excellent catalytic activity of 1 for the hydroboration of organic compounds with carbonyl groups was investigated. Furthermore, it was shown that 1 effectively initiates the addition reaction of trimethylsilyl cyanide (TMSCN) to both aldehydes and ketones. Quantum mechanical calculations were carried out to explore the reaction mechanism.

KW - aluminum

KW - homogeneous catalysis

KW - hydrides

KW - hydroboration

KW - hydrosilylation

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ER -

An Aluminum Hydride That Functions like a Transition-Metal Catalyst

Abstract

Keywords

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