Synthesis of a 1-Aryl-2,2-chlorosilyl(phospha)silene Coordinated by an N-Heterocyclic Carbene

Andreas Wolfgang Kyri; Paresh Kumar Majhi; Takahiro Sasamori; Tomohiro Agou; Vitaly Nesterov; Jing-Dong Guo; Shigeru Nagase; Norihiro Tokitoh; Rainer Streubel

doi:10.3390/molecules21101309

Synthesis of a 1-Aryl-2,2-chlorosilyl(phospha)silene Coordinated by an N-Heterocyclic Carbene

Molecules. 2016 Sep 30;21(10):1309. doi: 10.3390/molecules21101309.

Authors

Andreas Wolfgang Kyri^{1

2}, Paresh Kumar Majhi³, Takahiro Sasamori⁴, Tomohiro Agou⁵, Vitaly Nesterov^{6

7}, Jing-Dong Guo⁸, Shigeru Nagase⁹, Norihiro Tokitoh¹⁰, Rainer Streubel¹¹

Affiliations

¹ Institute for Chemical Research, Kyoto University, Gokasho, Uji, 611-0011 Kyoto, Japan. kyri@uni-bonn.de.
² Institut für Anorganische Chemie der Rheinischen Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany. kyri@uni-bonn.de.
³ Institute for Chemical Research, Kyoto University, Gokasho, Uji, 611-0011 Kyoto, Japan. pmajhi@boc.kuicr.kyoto-u.ac.jp.
⁴ Institute for Chemical Research, Kyoto University, Gokasho, Uji, 611-0011 Kyoto, Japan. sasamori@boc.kuicr.kyoto-u.ac.jp.
⁵ Institute for Chemical Research, Kyoto University, Gokasho, Uji, 611-0011 Kyoto, Japan. tomohiro.agou.mountain@vc.ibaraki.ac.jp.
⁶ Institute for Chemical Research, Kyoto University, Gokasho, Uji, 611-0011 Kyoto, Japan. v.nesterov@tum.de.
⁷ Institut für Anorganische Chemie der Rheinischen Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany. v.nesterov@tum.de.
⁸ Institute for Chemical Research, Kyoto University, Gokasho, Uji, 611-0011 Kyoto, Japan. guo_jd@boc.kuicr.kyoto-u.ac.jp.
⁹ Fukui Institute for Fundamental Chemistry, Kyoto University, 606-8103 Kyoto, Japan. nagase@ims.ac.jp.
¹⁰ Institute for Chemical Research, Kyoto University, Gokasho, Uji, 611-0011 Kyoto, Japan. tokitoh@boc.kuicr.kyoto-u.ac.jp.
¹¹ Institut für Anorganische Chemie der Rheinischen Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany. r.streubel@uni-bonn.de.

Abstract

Phosphasilenes, P=Si doubly bonded compounds, have received considerable attention due to their unique physical and chemical properties. We report on the synthesis and structure of a chlorophosphasilene coordinated by an N-heterocyclic carbene (NHC), which has the potential of functionalization at the Si-Cl moiety. Treatment of a silylphosphine, ArPH-SiCl₂R_Si (Ar = bulky aryl group, R_Si = Si(SiMe₃)₃) with two equivalents of Im-Me₄ (1,3,4,5-tetramethylimidazol-2-ylidene) afforded the corresponding NHC-coordinated phosphasilene, ArP=SiClR_Si(Im-Me₄) as a stable compound. Bonding properties of the P=Si bond coordinated to an NHC will be discussed on the basis of theoretical calculations.

Keywords: N-heterocyclic carbene; main group elements; phosphasilene.

MeSH terms

Heterocyclic Compounds, 1-Ring* / chemical synthesis
Heterocyclic Compounds, 1-Ring* / chemistry
Methane / analogs & derivatives*
Methane / chemical synthesis
Methane / chemistry
Silene / chemistry*

Substances

Heterocyclic Compounds, 1-Ring
carbene
Methane