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Reaction of Bis(alkynyl)silanes with Tris(pentafluorophenyl)borane: Synthesis of Bulky Silole Derivatives by Means of 1,1‐Carboboration under Mild Reaction Conditions
Author(s) -
Dierker Gereon,
Ugolotti Juri,
Kehr Gerald,
Fröhlich Roland,
Erker Gerhard
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900029
Subject(s) - chemistry , borane , medicinal chemistry , silane , derivative (finance) , boranes , tris , silanes , toluene , boron , lewis acids and bases , polymer chemistry , organic chemistry , catalysis , biochemistry , financial economics , economics
The strong Lewis acid tris(pentafluorophenyl)borane [B(C 6 F 5 ) 3 ] reacts rapidly with dimethylbis(phenylethynyl)silane ( 1c ) at room temperature in toluene by shift of a pentafluorophenyl (C 6 F 5 ) group and formation of a new carbon‐bis(pentafluorophenyl)boron linkage [CB(C 6 F 5 ) 2 ] in a sequence of 1,1‐carboboration reactions to yield the 4‐bis(pentafluorophenyl)boryl/3‐pentafluorophenyl‐substituted 1,1‐dimethyl‐2,5‐diphenylsilole derivative 7c . The analogous reaction of bis(trimethylsilylethynyl)diphenylsilane ( 1d ) with tris(pentafluorophenyl)borane gave the corresponding boryl‐substituted silole derivative ( 7d ) featuring six bulky substituents attached at the central heterocyclic framework. Both the starting materials ( 1c , 1d ) and the products ( 7c , 7d ) were characterized by X‐ray crystal structure analyses.