Synthesis of a Base-Stabilized Silicon(I)-Iron(II) Complex for Hydroboration of Carbonyl Compounds

Sabrina Khoo; Jiajia Cao; Fiona Ng; Cheuk Wai So

doi:10.1021/acs.inorgchem.8b01760

Synthesis of a Base-Stabilized Silicon(I)-Iron(II) Complex for Hydroboration of Carbonyl Compounds

Sabrina Khoo, Jiajia Cao, Fiona Ng, Cheuk Wai So^*

^*Corresponding author for this work

Nanyang Technological University

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

26 Citations (Scopus)

Abstract

The reaction of the amidinatosilicon(I) dimer [LSi:]₂ (1; L = PhC(NtBu)₂) with FeBr₂ in tetrahydrofuran (THF) at ambient temperature afforded the silicon(I)-iron(II) dimer [LSi(FeBr₂·THF)]₂ (2) after 40 h. Compound 2 can catalyze hydroboration of aliphatic and aromatic ketone compounds with HBpin in the absence of any strong reducing agent. Mechanistic studies show that complex 2 reacts with ketone compounds to form a zwitterionic intermediate in the first step of catalysis. Subsequent reaction with HBpin affords the corresponding boron esters and then regenerates complex 2.

Original language	English
Pages (from-to)	12452-12455
Number of pages	4
Journal	Inorganic Chemistry
Volume	57
Issue number	20
DOIs	https://doi.org/10.1021/acs.inorgchem.8b01760
Publication status	Published - Oct 15 2018
Externally published	Yes

Bibliographical note

Publisher Copyright:
Copyright © 2018 American Chemical Society.

ASJC Scopus Subject Areas

Physical and Theoretical Chemistry
Inorganic Chemistry

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10.1021/acs.inorgchem.8b01760

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title = "Synthesis of a Base-Stabilized Silicon(I)-Iron(II) Complex for Hydroboration of Carbonyl Compounds",

abstract = "The reaction of the amidinatosilicon(I) dimer [LSi:]2 (1; L = PhC(NtBu)2) with FeBr2 in tetrahydrofuran (THF) at ambient temperature afforded the silicon(I)-iron(II) dimer [LSi(FeBr2·THF)]2 (2) after 40 h. Compound 2 can catalyze hydroboration of aliphatic and aromatic ketone compounds with HBpin in the absence of any strong reducing agent. Mechanistic studies show that complex 2 reacts with ketone compounds to form a zwitterionic intermediate in the first step of catalysis. Subsequent reaction with HBpin affords the corresponding boron esters and then regenerates complex 2.",

author = "Sabrina Khoo and Jiajia Cao and Fiona Ng and So, {Cheuk Wai}",

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AU - Khoo, Sabrina

AU - Cao, Jiajia

AU - Ng, Fiona

AU - So, Cheuk Wai

PY - 2018/10/15

Y1 - 2018/10/15

N2 - The reaction of the amidinatosilicon(I) dimer [LSi:]2 (1; L = PhC(NtBu)2) with FeBr2 in tetrahydrofuran (THF) at ambient temperature afforded the silicon(I)-iron(II) dimer [LSi(FeBr2·THF)]2 (2) after 40 h. Compound 2 can catalyze hydroboration of aliphatic and aromatic ketone compounds with HBpin in the absence of any strong reducing agent. Mechanistic studies show that complex 2 reacts with ketone compounds to form a zwitterionic intermediate in the first step of catalysis. Subsequent reaction with HBpin affords the corresponding boron esters and then regenerates complex 2.

AB - The reaction of the amidinatosilicon(I) dimer [LSi:]2 (1; L = PhC(NtBu)2) with FeBr2 in tetrahydrofuran (THF) at ambient temperature afforded the silicon(I)-iron(II) dimer [LSi(FeBr2·THF)]2 (2) after 40 h. Compound 2 can catalyze hydroboration of aliphatic and aromatic ketone compounds with HBpin in the absence of any strong reducing agent. Mechanistic studies show that complex 2 reacts with ketone compounds to form a zwitterionic intermediate in the first step of catalysis. Subsequent reaction with HBpin affords the corresponding boron esters and then regenerates complex 2.

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Synthesis of a Base-Stabilized Silicon(I)-Iron(II) Complex for Hydroboration of Carbonyl Compounds

Abstract

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