Addition Reactions of Me3SiCN with Aldehydes Catalyzed by Aluminum Complexes Containing in their Coordination Sphere O, S, and N Ligands

Zhi Yang; Yafei Yi; Mingdong Zhong; Sriman De; Totan Mondal; Debasis Koley; Xiaoli Ma; Dongxiang Zhang; Herbert W. Roesky

doi:10.1002/chem.201505162

Addition Reactions of Me₃SiCN with Aldehydes Catalyzed by Aluminum Complexes Containing in their Coordination Sphere O, S, and N Ligands

Zhi Yang^*, Yafei Yi, Mingdong Zhong, Sriman De, Totan Mondal, Debasis Koley, Xiaoli Ma, Dongxiang Zhang, Herbert W. Roesky

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

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

29 Citations (Scopus)

Abstract

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).

Original language	English
Pages (from-to)	6932-6938
Number of pages	7
Journal	Chemistry - A European Journal
Volume	22
Issue number	20
DOIs	https://doi.org/10.1002/chem.201505162
Publication status	Published - 10 May 2016

Keywords

DFT studies
Lewis acid catalyst
addition reactions
aluminum complexes

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10.1002/chem.201505162

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@article{f66aff007c7e4b469f8515e92b8ea45c,

title = "Addition Reactions of Me3SiCN with Aldehydes Catalyzed by Aluminum Complexes Containing in their Coordination Sphere O, S, and N Ligands",

abstract = "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).",

keywords = "DFT studies, Lewis acid catalyst, addition reactions, aluminum complexes",

author = "Zhi Yang and Yafei Yi and Mingdong Zhong and Sriman De and Totan Mondal and Debasis Koley and Xiaoli Ma and Dongxiang Zhang and Roesky, {Herbert W.}",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2016",

month = may,

day = "10",

doi = "10.1002/chem.201505162",

language = "English",

volume = "22",

pages = "6932--6938",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "20",

}

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.

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 -

Addition Reactions of Me₃SiCN with Aldehydes Catalyzed by Aluminum Complexes Containing in their Coordination Sphere O, S, and N Ligands

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