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An Aluminum Hydride That Functions like a Transition‐Metal Catalyst
Author(s) -
Yang Zhi,
Zhong Mingdong,
Ma Xiaoli,
De Susmita,
Anusha Chakkittakandiyil,
Parameswaran Pattiyil,
Roesky Herbert W.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201503304
Subject(s) - chemistry , catalysis , trimethylsilyl cyanide , substituent , trifluoromethanesulfonate , hydroboration , yield (engineering) , trimethylsilyl , transition metal , medicinal chemistry , hydride , lewis acids and bases , aldehyde , photochemistry , metal , organic chemistry , materials science , metallurgy
The reaction of [LAlH 2 ] (L=HC(CMeNAr) 2 , Ar=2,6‐ i Pr 2 C 6 H 3 ) with MeOTf (Tf=SO 2 CF 3 ) 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.