[Mes--TMP] borinium cation initiated cyanosilylation and catalysed hydrosilylation of ketones and aldehydes

Two aryl amino borinium cations derived from Cl(Mes)B-NR 2 (NR 2 = TMP, HMDS) faced divergent outcomes. As the HMDS-substituted one underwent methyl migration from silicon to boron transforming the putative borinium ion to a silylium ion, [Mes- B -TMP] + can initiate cyanosilylation and catalyse hyd...

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Published inChemical communications (Cambridge, England) Vol. 57; no. 1; pp. 13732 - 13735
Main Authors Chen, Po-Han, Hsu, Ching-Pei, Tseng, Hsi-Ching, Liu, Yi-Hung, Chiu, Ching-Wen
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 16.12.2021
Royal Society of Chemistry
Subjects
Aldehydes
Cations
Chemistry
Chemistry, Multidisciplinary
Hydrosilylation
Ketones
Physical Sciences
Science & Technology
STEREOSELECTIVE ALDOL CONDENSATIONS
HYDROBORATION
BORON
TRIS(PENTAFLUOROPHENYL)BORANE
IMINES
CHEMISTRY
CARBONYL-COMPOUNDS
CONVENIENT
ION
BORENIUM
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Summary:Two aryl amino borinium cations derived from Cl(Mes)B-NR 2 (NR 2 = TMP, HMDS) faced divergent outcomes. As the HMDS-substituted one underwent methyl migration from silicon to boron transforming the putative borinium ion to a silylium ion, [Mes- B -TMP] + can initiate cyanosilylation and catalyse hydrosilylation of ketones and aldehydes. Aryl amino borinium cation can serve as the catalyst for hydrosilylation of ketones and aldehydes.
Bibliography:Electronic supplementary information (ESI) available. CCDC
For ESI and crystallographic data in CIF or other electronic format see DOI
2120764
2120765
and
2120763
,
10.1039/d1cc06319g
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc06319g