TY - JOUR
T1 - Addition Reactions of Me3SiCN with Aldehydes Catalyzed by Aluminum Complexes Containing in their Coordination Sphere O, S, and N Ligands
AU - Yang, Zhi
AU - Yi, Yafei
AU - Zhong, Mingdong
AU - De, Sriman
AU - Mondal, Totan
AU - Koley, Debasis
AU - Ma, Xiaoli
AU - Zhang, Dongxiang
AU - Roesky, Herbert W.
N1 - Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2016/5/10
Y1 - 2016/5/10
N2 - The reaction of one equivalent of LAlH2 (1; L=HC(CMeNAr)2, Ar=2,6-iPr2C6H3, β-diketiminate ligand) with two equivalents of 2-mercapto-4,6-dimethylpyrimidine hydrate resulted in LAl[(μ-S)(m-C4N2H)(CH2)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-C6H4)CN(C5NH4)]2 (3), LAlH[(μ-O)(o-C4H4)CN(2,6-iPr2C6H3)] (4), and LAl[(μ-NH)(o-C8SH8)(COOC2H5)]2 (5) were isolated. Compounds 2-5 were characterized by 1H and 13C 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).
AB - The reaction of one equivalent of LAlH2 (1; L=HC(CMeNAr)2, Ar=2,6-iPr2C6H3, β-diketiminate ligand) with two equivalents of 2-mercapto-4,6-dimethylpyrimidine hydrate resulted in LAl[(μ-S)(m-C4N2H)(CH2)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-C6H4)CN(C5NH4)]2 (3), LAlH[(μ-O)(o-C4H4)CN(2,6-iPr2C6H3)] (4), and LAl[(μ-NH)(o-C8SH8)(COOC2H5)]2 (5) were isolated. Compounds 2-5 were characterized by 1H and 13C 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).
KW - DFT studies
KW - Lewis acid catalyst
KW - addition reactions
KW - aluminum complexes
UR - http://www.scopus.com/inward/record.url?scp=84981763951&partnerID=8YFLogxK
U2 - 10.1002/chem.201505162
DO - 10.1002/chem.201505162
M3 - Article
AN - SCOPUS:84981763951
SN - 0947-6539
VL - 22
SP - 6932
EP - 6938
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 20
ER -