A facile and selective route to remarkably inert monocyclic NHC-stabilized boriranes

Holger Braunschweig; Christina Claes; Alexander Damme; Andrea Deißenberger; Rian D. Dewhurst; Christian Hörl; Thomas Kramer

doi:10.1039/c4cc09036e

A facile and selective route to remarkably inert monocyclic NHC-stabilized boriranes

Holger Braunschweig^*, Christina Claes, Alexander Damme, Andrea Deißenberger, Rian D. Dewhurst, Christian Hörl, Thomas Kramer

^*Corresponding author for this work

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

38 Citations (Scopus)

Abstract

Herein we report a facile and selective synthetic route to monocyclic NHC-stabilized boriranes. We have succeeded in obtaining two highly stable new boriranes through salt elimination of NHC-stabilized dichloroboranes with the dianion of trans-stilbene, Na₂[C₁₄H₁₂]. One borirane was observed to undergo reaction with [Pt(PEt₃)₃], in which the Pt(0) center oxidatively adds a backbone C-H bond of the NHC, leading to the isolation of the Pt(ii) complex trans-[(Et₃P)₂PtH{C=CH(NMe)₂C·BPh(C₁₄H₁₂)}]. The remarkable inertness of the NHC-boriranes suggests a strong stabilising effect of quaternization of the boron atom.

Original language	English
Pages (from-to)	1627-1630
Number of pages	4
Journal	Chemical Communications
Volume	51
Issue number	9
DOIs	https://doi.org/10.1039/c4cc09036e
Publication status	Published - 31 Jan 2015
Externally published	Yes

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title = "A facile and selective route to remarkably inert monocyclic NHC-stabilized boriranes",

abstract = "Herein we report a facile and selective synthetic route to monocyclic NHC-stabilized boriranes. We have succeeded in obtaining two highly stable new boriranes through salt elimination of NHC-stabilized dichloroboranes with the dianion of trans-stilbene, Na2[C14H12]. One borirane was observed to undergo reaction with [Pt(PEt3)3], in which the Pt(0) center oxidatively adds a backbone C-H bond of the NHC, leading to the isolation of the Pt(ii) complex trans-[(Et3P)2PtH{C=CH(NMe)2C·BPh(C14H12)}]. The remarkable inertness of the NHC-boriranes suggests a strong stabilising effect of quaternization of the boron atom.",

author = "Holger Braunschweig and Christina Claes and Alexander Damme and Andrea Dei{\ss}enberger and Dewhurst, {Rian D.} and Christian H{\"o}rl and Thomas Kramer",

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T1 - A facile and selective route to remarkably inert monocyclic NHC-stabilized boriranes

AU - Braunschweig, Holger

AU - Claes, Christina

AU - Damme, Alexander

AU - Deißenberger, Andrea

AU - Dewhurst, Rian D.

AU - Hörl, Christian

AU - Kramer, Thomas

PY - 2015/1/31

Y1 - 2015/1/31

N2 - Herein we report a facile and selective synthetic route to monocyclic NHC-stabilized boriranes. We have succeeded in obtaining two highly stable new boriranes through salt elimination of NHC-stabilized dichloroboranes with the dianion of trans-stilbene, Na2[C14H12]. One borirane was observed to undergo reaction with [Pt(PEt3)3], in which the Pt(0) center oxidatively adds a backbone C-H bond of the NHC, leading to the isolation of the Pt(ii) complex trans-[(Et3P)2PtH{C=CH(NMe)2C·BPh(C14H12)}]. The remarkable inertness of the NHC-boriranes suggests a strong stabilising effect of quaternization of the boron atom.

AB - Herein we report a facile and selective synthetic route to monocyclic NHC-stabilized boriranes. We have succeeded in obtaining two highly stable new boriranes through salt elimination of NHC-stabilized dichloroboranes with the dianion of trans-stilbene, Na2[C14H12]. One borirane was observed to undergo reaction with [Pt(PEt3)3], in which the Pt(0) center oxidatively adds a backbone C-H bond of the NHC, leading to the isolation of the Pt(ii) complex trans-[(Et3P)2PtH{C=CH(NMe)2C·BPh(C14H12)}]. The remarkable inertness of the NHC-boriranes suggests a strong stabilising effect of quaternization of the boron atom.

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U2 - 10.1039/c4cc09036e

DO - 10.1039/c4cc09036e

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EP - 1630

JO - Chemical Communications

JF - Chemical Communications

IS - 9

ER -

A facile and selective route to remarkably inert monocyclic NHC-stabilized boriranes

Abstract

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