Borane-catalyzed cross-metathesis strategy for facile transformation of cyclic (alkyl)(amino)germylenes

A borane B(C6 F5 )3 -catalyzed metathesis reaction between the Si-C bond in the cyclic (alkyl)(amino)germylene (CAAGe) 1 and the Si-H bond in a silane (R3 SiH; 2) is reported. Mechanistic studies propose that the initial step of the reaction involves Si-H bond activation to furnish an ionic species...

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Main Authors: Rao, Bin, Wang, Liliang, Kinjo, Rei
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2021
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Online Access:https://hdl.handle.net/10356/146199
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spelling sg-ntu-dr.10356-1461992023-02-28T19:30:06Z Borane-catalyzed cross-metathesis strategy for facile transformation of cyclic (alkyl)(amino)germylenes Rao, Bin Wang, Liliang Kinjo, Rei School of Physical and Mathematical Sciences Science::Chemistry Borane Germylene A borane B(C6 F5 )3 -catalyzed metathesis reaction between the Si-C bond in the cyclic (alkyl)(amino)germylene (CAAGe) 1 and the Si-H bond in a silane (R3 SiH; 2) is reported. Mechanistic studies propose that the initial step of the reaction involves Si-H bond activation to furnish an ionic species [1-SiR3 ]+ [HB(C6 F5 )3 ]- , from which [Me3 Si]+ [HB(C6 F5 )3 ]- and an azagermole intermediate are generated. The former yields Me3 SiH concomitant with the regeneration of B(C6 F5 )3 whereas the latter undergoes isomerization to afford CAAGes bearing various silyl groups on the carbon atom next to the germylene center. This strategy allows the straightforward synthesis of eight new CAAGes starting from 1. Ministry of Education (MOE) Nanyang Technological University Accepted version We are grateful to the Nanyang Technological University (NTU) and Ministry of Education, Singapore (MOE2015-T1-001-029:RG9/15) for financial support. We also like to thank Dr. Li Yongxin (NTU) for assistance in X-ray crystallographic analysis. 2021-02-01T08:29:23Z 2021-02-01T08:29:23Z 2019 Journal Article Rao, B., Wang, L., & Kinjo, R. (2019). Borane-catalyzed cross-metathesis strategy for facile transformation of cyclic (alkyl)(amino)germylenes. Angewandte Chemie International Edition, 58(1), 231-235. doi:10.1002/anie.201811574 1433-7851 https://hdl.handle.net/10356/146199 10.1002/anie.201811574 30447043 2-s2.0-85058029715 1 58 231 235 en Angewandte Chemie International Edition This is the accepted version of the following article: Rao, B., Wang, L., & Kinjo, R. (2019). Borane-catalyzed cross-metathesis strategy for facile transformation of cyclic (alkyl)(amino)germylenes. Angewandte Chemie International Edition, 58(1), 231-235. doi:10.1002/anie.201811574, which has been published in final form at https://doi.org/10.1002/anie.201811574. This article may be used for non-commercial purposes in accordance with the Wiley Self-Archiving Policy [https://authorservices.wiley.com/authorresources/Journal-Authors/licensing/self-archiving.html]. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry
Borane
Germylene
spellingShingle Science::Chemistry
Borane
Germylene
Rao, Bin
Wang, Liliang
Kinjo, Rei
Borane-catalyzed cross-metathesis strategy for facile transformation of cyclic (alkyl)(amino)germylenes
description A borane B(C6 F5 )3 -catalyzed metathesis reaction between the Si-C bond in the cyclic (alkyl)(amino)germylene (CAAGe) 1 and the Si-H bond in a silane (R3 SiH; 2) is reported. Mechanistic studies propose that the initial step of the reaction involves Si-H bond activation to furnish an ionic species [1-SiR3 ]+ [HB(C6 F5 )3 ]- , from which [Me3 Si]+ [HB(C6 F5 )3 ]- and an azagermole intermediate are generated. The former yields Me3 SiH concomitant with the regeneration of B(C6 F5 )3 whereas the latter undergoes isomerization to afford CAAGes bearing various silyl groups on the carbon atom next to the germylene center. This strategy allows the straightforward synthesis of eight new CAAGes starting from 1.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Rao, Bin
Wang, Liliang
Kinjo, Rei
format Article
author Rao, Bin
Wang, Liliang
Kinjo, Rei
author_sort Rao, Bin
title Borane-catalyzed cross-metathesis strategy for facile transformation of cyclic (alkyl)(amino)germylenes
title_short Borane-catalyzed cross-metathesis strategy for facile transformation of cyclic (alkyl)(amino)germylenes
title_full Borane-catalyzed cross-metathesis strategy for facile transformation of cyclic (alkyl)(amino)germylenes
title_fullStr Borane-catalyzed cross-metathesis strategy for facile transformation of cyclic (alkyl)(amino)germylenes
title_full_unstemmed Borane-catalyzed cross-metathesis strategy for facile transformation of cyclic (alkyl)(amino)germylenes
title_sort borane-catalyzed cross-metathesis strategy for facile transformation of cyclic (alkyl)(amino)germylenes
publishDate 2021
url https://hdl.handle.net/10356/146199
_version_ 1759857285707857920