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Addition Reactions of Me 3 SiCN with Aldehydes Catalyzed by Aluminum Complexes Containing in their Coordination Sphere O, S, and N Ligands
Author(s) -
Yang Zhi,
Yi Yafei,
Zhong Mingdong,
De Sriman,
Mondal Totan,
Koley Debasis,
Ma Xiaoli,
Zhang Dongxiang,
Roesky Herbert W.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201505162
Subject(s) - trimethylsilyl cyanide , chemistry , hydrate , catalysis , ligand (biochemistry) , coordination sphere , carboxylate , yield (engineering) , medicinal chemistry , trimethylsilyl , cyanide , crystal structure , nuclear magnetic resonance spectroscopy , stereochemistry , crystallography , inorganic chemistry , organic chemistry , materials science , biochemistry , receptor , metallurgy
The reaction of one equivalent of LAlH 2 ( 1 ; L=HC(CMeNAr) 2 , Ar=2,6‐ i Pr 2 C 6 H 3 , β‐diketiminate ligand) with two equivalents of 2‐mercapto‐4,6‐dimethylpyrimidine hydrate resulted in LAl[(μ‐S)( m ‐C 4 N 2 H)(CH 2 ) 2 ] 2 ( 2 ) in good yield. Similarly, when N ‐2‐pyridylsalicylideneamine, N ‐(2,6‐diisopropylphenyl)salicylaldimine, and ethyl 3‐amino‐4,5,6,7‐tetrahydrobenzo[ b ]thiophene‐2‐carboxylate were used as starting materials, the corresponding products LAl[(μ‐O)( o ‐C 6 H 4 )CN(C 5 NH 4 )] 2 ( 3 ), LAlH[(μ‐O)( o ‐C 4 H 4 )CN(2,6‐ i Pr 2 C 6 H 3 )] ( 4 ), and LAl[(μ‐NH)( o ‐C 8 SH 8 )(COOC 2 H 5 )] 2 ( 5 ) were isolated. Compounds 2 – 5 were characterized by 1 H and 13 C NMR spectroscopy as well as by single‐crystal X‐ray structural analysis. Surprisingly, compounds 2 – 5 exhibit good catalytic activity in addition reactions of aldehydes with trimethylsilyl cyanide (TMSCN).