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The Propargyl Rearrangement to Functionalised Allyl‐Boron and Borocation Compounds
Author(s) -
Wilkins Lewis C.,
Lawson James R.,
Wieneke Philipp,
Rominger Frank,
Hashmi A. Stephen K.,
Hansmann Max M.,
Melen Rebecca L.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201602719
Subject(s) - boranes , propargyl , chemistry , boron , yield (engineering) , medicinal chemistry , alkyl , aryl , carbon fibers , organic chemistry , catalysis , materials science , composite number , metallurgy , composite material
A diverse range of Lewis acidic alkyl, vinyl and aryl boranes and borenium compounds that are capable of new carbon–carbon bond formation through selective migratory group transfer have been synthesised. Utilising a series of heteroleptic boranes [PhB(C 6 F 5 ) 2 ( 1 ), PhCH 2 CH 2 B(C 6 F 5 ) 2 ( 2 ), and E ‐B(C 6 F 5 ) 2 (C 6 F 5 )C=C(I)R (R=Ph 3 a , n Bu 3 b )] and borenium cations [phenylquinolatoborenium cation ([QOBPh][AlCl 4 ], 4 )], it has been shown that these boron‐based compounds are capable of producing novel allyl‐ boron and boronium compounds through complex rearrangement reactions with various propargyl esters and carbamates. These reactions yield highly functionalised, synthetically useful boron substituted organic compounds with substantial molecular complexity in a one‐pot reaction.