From Borane to Borylene without Reduction: Ambiphilic Behavior of a Monovalent Silylisonitrile Boron Species

Merle Arrowsmith; Dominic Auerhammer; Rüdiger Bertermann; Holger Braunschweig; Mehmet Ali Celik; Julian Erdmannsdörfer; Ivo Krummenacher; Thomas Kupfer

doi:10.1002/anie.201705561

From Borane to Borylene without Reduction: Ambiphilic Behavior of a Monovalent Silylisonitrile Boron Species

Angew Chem Int Ed Engl. 2017 Sep 4;56(37):11263-11267. doi: 10.1002/anie.201705561. Epub 2017 Jul 17.

Authors

Merle Arrowsmith^{1

2}, Dominic Auerhammer^{1

2}, Rüdiger Bertermann^{1

2}, Holger Braunschweig^{1

2}, Mehmet Ali Celik¹, Julian Erdmannsdörfer^{1

2}, Ivo Krummenacher^{1

2}, Thomas Kupfer^{1

2}

Affiliations

¹ Institut für Anorganische Chemie, Julius-Maximilians Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
² The Institute for Sustainable Chemistry & Catalysis with Boron, Julius-Maximilians Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.

PMID: 28640395
DOI: 10.1002/anie.201705561

Abstract

Deprotonation of [(cAAC)BH₂ (CN)] provided clean access to the stable boryl anion, [(cAAC)BH(CN)]^- . Whereas the addition of soft electrophiles occurred at the nucleophilic boron center, harder silyl electrophiles added to the harder terminal cyano nitrogen. The resulting [(cAAC)BH(CNSiPh₃ )] species behaved like a silylium boryl nucleophile as well as a neutral silylisonitrile borylene.

Keywords: Group 14 elements; ambiphilic reactivity; boryl anions; borylenes; umpolung.

Publication types

Research Support, Non-U.S. Gov't