Hydroboration of Aldehydes, Ketones, and Carbodiimides Promoted by Mono(imidazolin-2-iminato) Hafnium Complexes

Maxim Khononov; Natalia Fridman; Matthias Tamm; Moris S. Eisen

doi:10.1002/ejoc.201901750

Hydroboration of Aldehydes, Ketones, and Carbodiimides Promoted by Mono(imidazolin-2-iminato) Hafnium Complexes

Maxim Khononov, Natalia Fridman, Matthias Tamm^*, Moris S. Eisen^*

^*Corresponding author for this work

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

23 Scopus citations

Abstract

Imidazolin-2-iminato hafnium complexes of the type [(Im^RN)Hf(CH₂Ph)₃] were synthesized (Im^tBuN = 1,3-di-tert-butylimidazolin-2-iminato); Im^DippN = 1,3-bis(2,6-diisopropylphenyl)-imidazolin-2-iminato. The complexes were crystallized and structurally characterized. Despite the oxophilicity of the hafnium center, both hafnium complexes were catalytically active in the hydroboration of aldehydes, ketones, and carbodiimides. Herein, we present the influence of different substrates bearing electron-withdrawing or electron-donating groups on the catalytic reactions. Based on stoichiometric reaction in each process, plausible mechanistic scenarios are presented.

Original language	English
Pages (from-to)	3153-3160
Number of pages	8
Journal	European Journal of Organic Chemistry
Volume	2020
Issue number	21
DOIs	https://doi.org/10.1002/ejoc.201901750
State	Published - 8 Jun 2020
Externally published	Yes

Keywords

Aldehydes
Carbodiimides
Hafnium-hydride
Hydroboration
Ketones

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10.1002/ejoc.201901750

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@article{f13e0e765e964863b01f1fad858665a1,

title = "Hydroboration of Aldehydes, Ketones, and Carbodiimides Promoted by Mono(imidazolin-2-iminato) Hafnium Complexes",

abstract = "Imidazolin-2-iminato hafnium complexes of the type [(ImRN)Hf(CH2Ph)3] were synthesized (ImtBuN = 1,3-di-tert-butylimidazolin-2-iminato); ImDippN = 1,3-bis(2,6-diisopropylphenyl)-imidazolin-2-iminato. The complexes were crystallized and structurally characterized. Despite the oxophilicity of the hafnium center, both hafnium complexes were catalytically active in the hydroboration of aldehydes, ketones, and carbodiimides. Herein, we present the influence of different substrates bearing electron-withdrawing or electron-donating groups on the catalytic reactions. Based on stoichiometric reaction in each process, plausible mechanistic scenarios are presented.",

keywords = "Aldehydes, Carbodiimides, Hafnium-hydride, Hydroboration, Ketones",

author = "Maxim Khononov and Natalia Fridman and Matthias Tamm and Eisen, {Moris S.}",

note = "Publisher Copyright: {\textcopyright} 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.",

year = "2020",

month = jun,

day = "8",

doi = "10.1002/ejoc.201901750",

language = "英语",

volume = "2020",

pages = "3153--3160",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

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TY - JOUR

T1 - Hydroboration of Aldehydes, Ketones, and Carbodiimides Promoted by Mono(imidazolin-2-iminato) Hafnium Complexes

AU - Khononov, Maxim

AU - Fridman, Natalia

AU - Tamm, Matthias

AU - Eisen, Moris S.

PY - 2020/6/8

Y1 - 2020/6/8

N2 - Imidazolin-2-iminato hafnium complexes of the type [(ImRN)Hf(CH2Ph)3] were synthesized (ImtBuN = 1,3-di-tert-butylimidazolin-2-iminato); ImDippN = 1,3-bis(2,6-diisopropylphenyl)-imidazolin-2-iminato. The complexes were crystallized and structurally characterized. Despite the oxophilicity of the hafnium center, both hafnium complexes were catalytically active in the hydroboration of aldehydes, ketones, and carbodiimides. Herein, we present the influence of different substrates bearing electron-withdrawing or electron-donating groups on the catalytic reactions. Based on stoichiometric reaction in each process, plausible mechanistic scenarios are presented.

AB - Imidazolin-2-iminato hafnium complexes of the type [(ImRN)Hf(CH2Ph)3] were synthesized (ImtBuN = 1,3-di-tert-butylimidazolin-2-iminato); ImDippN = 1,3-bis(2,6-diisopropylphenyl)-imidazolin-2-iminato. The complexes were crystallized and structurally characterized. Despite the oxophilicity of the hafnium center, both hafnium complexes were catalytically active in the hydroboration of aldehydes, ketones, and carbodiimides. Herein, we present the influence of different substrates bearing electron-withdrawing or electron-donating groups on the catalytic reactions. Based on stoichiometric reaction in each process, plausible mechanistic scenarios are presented.

KW - Aldehydes

KW - Carbodiimides

KW - Hafnium-hydride

KW - Hydroboration

KW - Ketones

UR - http://www.scopus.com/inward/record.url?scp=85079837953&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201901750

DO - 10.1002/ejoc.201901750

M3 - 文章

AN - SCOPUS:85079837953

SN - 1434-193X

VL - 2020

SP - 3153

EP - 3160

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 21

ER -

Hydroboration of Aldehydes, Ketones, and Carbodiimides Promoted by Mono(imidazolin-2-iminato) Hafnium Complexes

Abstract

Keywords

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