Reaction of Dihalodiboranes(4) with a N-Heterocyclic Silylene: Facile Construction of 1-Aryl-2-Silyl-1,2-Diboraindanes

Holger Braunschweig; Tobias Brückner; Andrea Deißenberger; Rian D. Dewhurst; Annika Gackstatter; Annalena Gärtner; Alexander Hofmann; Thomas Kupfer; Dominic Prieschl; Torsten Thiess; Sunewang Rixin Wang

doi:10.1002/chem.201702377

Reaction of Dihalodiboranes(4) with a N-Heterocyclic Silylene: Facile Construction of 1-Aryl-2-Silyl-1,2-Diboraindanes

Holger Braunschweig^*
, Tobias Brückner
, Andrea Deißenberger
, Rian D. Dewhurst
, Annika Gackstatter
, Annalena Gärtner
, Alexander Hofmann
, Thomas Kupfer
, Dominic Prieschl
, Torsten Thiess
, Sunewang Rixin Wang

^*Corresponding author for this work

University of Würzburg

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

24 Scopus citations

Abstract

Dihalodiboranes(4) react with a N-heterocyclic silylene (NHSi) to generate NHSi adducts of 1-aryl-2-silyl-1,2-diboraindanes, as was confirmed by X-ray crystallography, featuring the functionalization of both B−X (X=halogen) bonds and a sp³- or sp²-C−H bond under mild conditions. Coordination of a third NHSi to the proposed 1,1-diaryl-2,2-disilyldiborane(4) intermediates, generated by a twofold B−X insertion, may be crucial for the C−H borylation that leads to the final products. Notably, our results demonstrate the first C−H borylation with a strong B−F bond activated by silylene insertion.

Original language	English
Pages (from-to)	9491-9494
Number of pages	4
Journal	Chemistry - A European Journal
Volume	23
Issue number	40
DOIs	https://doi.org/10.1002/chem.201702377
State	Published - 18 Jul 2017
Externally published	Yes

Keywords

bond activation
borylation
diboraindanes
diboranes
synthetic methods

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10.1002/chem.201702377

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Braunschweig, H., Brückner, T., Deißenberger, A., Dewhurst, R. D., Gackstatter, A., Gärtner, A., Hofmann, A., Kupfer, T., Prieschl, D., Thiess, T., & Wang, S. R. (2017). Reaction of Dihalodiboranes(4) with a N-Heterocyclic Silylene: Facile Construction of 1-Aryl-2-Silyl-1,2-Diboraindanes. Chemistry - A European Journal, 23(40), 9491-9494. https://doi.org/10.1002/chem.201702377

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title = "Reaction of Dihalodiboranes(4) with a N-Heterocyclic Silylene: Facile Construction of 1-Aryl-2-Silyl-1,2-Diboraindanes",

abstract = "Dihalodiboranes(4) react with a N-heterocyclic silylene (NHSi) to generate NHSi adducts of 1-aryl-2-silyl-1,2-diboraindanes, as was confirmed by X-ray crystallography, featuring the functionalization of both B−X (X=halogen) bonds and a sp3- or sp2-C−H bond under mild conditions. Coordination of a third NHSi to the proposed 1,1-diaryl-2,2-disilyldiborane(4) intermediates, generated by a twofold B−X insertion, may be crucial for the C−H borylation that leads to the final products. Notably, our results demonstrate the first C−H borylation with a strong B−F bond activated by silylene insertion.",

keywords = "bond activation, borylation, diboraindanes, diboranes, synthetic methods",

author = "Holger Braunschweig and Tobias Br{\"u}ckner and Andrea Dei{\ss}enberger and Dewhurst, \{Rian D.\} and Annika Gackstatter and Annalena G{\"a}rtner and Alexander Hofmann and Thomas Kupfer and Dominic Prieschl and Torsten Thiess and Wang, \{Sunewang Rixin\}",

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year = "2017",

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doi = "10.1002/chem.201702377",

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Braunschweig, H, Brückner, T, Deißenberger, A, Dewhurst, RD, Gackstatter, A, Gärtner, A, Hofmann, A, Kupfer, T, Prieschl, D, Thiess, T & Wang, SR 2017, 'Reaction of Dihalodiboranes(4) with a N-Heterocyclic Silylene: Facile Construction of 1-Aryl-2-Silyl-1,2-Diboraindanes', Chemistry - A European Journal, vol. 23, no. 40, pp. 9491-9494. https://doi.org/10.1002/chem.201702377

TY - JOUR

T1 - Reaction of Dihalodiboranes(4) with a N-Heterocyclic Silylene

T2 - Facile Construction of 1-Aryl-2-Silyl-1,2-Diboraindanes

AU - Braunschweig, Holger

AU - Brückner, Tobias

AU - Deißenberger, Andrea

AU - Dewhurst, Rian D.

AU - Gackstatter, Annika

AU - Gärtner, Annalena

AU - Hofmann, Alexander

AU - Kupfer, Thomas

AU - Prieschl, Dominic

AU - Thiess, Torsten

AU - Wang, Sunewang Rixin

PY - 2017/7/18

Y1 - 2017/7/18

N2 - Dihalodiboranes(4) react with a N-heterocyclic silylene (NHSi) to generate NHSi adducts of 1-aryl-2-silyl-1,2-diboraindanes, as was confirmed by X-ray crystallography, featuring the functionalization of both B−X (X=halogen) bonds and a sp3- or sp2-C−H bond under mild conditions. Coordination of a third NHSi to the proposed 1,1-diaryl-2,2-disilyldiborane(4) intermediates, generated by a twofold B−X insertion, may be crucial for the C−H borylation that leads to the final products. Notably, our results demonstrate the first C−H borylation with a strong B−F bond activated by silylene insertion.

AB - Dihalodiboranes(4) react with a N-heterocyclic silylene (NHSi) to generate NHSi adducts of 1-aryl-2-silyl-1,2-diboraindanes, as was confirmed by X-ray crystallography, featuring the functionalization of both B−X (X=halogen) bonds and a sp3- or sp2-C−H bond under mild conditions. Coordination of a third NHSi to the proposed 1,1-diaryl-2,2-disilyldiborane(4) intermediates, generated by a twofold B−X insertion, may be crucial for the C−H borylation that leads to the final products. Notably, our results demonstrate the first C−H borylation with a strong B−F bond activated by silylene insertion.

KW - bond activation

KW - borylation

KW - diboraindanes

KW - diboranes

KW - synthetic methods

UR - https://www.scopus.com/pages/publications/85021769175

U2 - 10.1002/chem.201702377

DO - 10.1002/chem.201702377

M3 - 文章

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AN - SCOPUS:85021769175

SN - 0947-6539

VL - 23

SP - 9491

EP - 9494

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 40

ER -

Reaction of Dihalodiboranes(4) with a N-Heterocyclic Silylene: Facile Construction of 1-Aryl-2-Silyl-1,2-Diboraindanes

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Keywords

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