The Propargyl Rearrangement to Functionalised Allyl‐Boron and Borocation Compounds |
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| Authors: | Lewis C Wilkins Dr James R Lawson Philipp Wieneke Frank Rominger Prof?Dr A Stephen K Hashmi Dr Max M Hansmann Dr Rebecca L Melen |
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| Institution: | 1. School of Chemistry, Main Building, Cardiff University, Cardiff, UK;2. Organisch-Chemisches Institut, Ruprecht-Karls-Universit?t Heidelberg, Heidelberg, Germany;3. Chemistry Department, Faculty of Science, King Abdulaziz University (KAU), Jeddah, Saudi Arabia |
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| Abstract: | 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(C6F5)2 ( 1 ), PhCH2CH2B(C6F5)2 ( 2 ), and E‐B(C6F5)2(C6F5)C=C(I)R (R=Ph 3 a , nBu 3 b )] and borenium cations phenylquinolatoborenium cation (QOBPh]AlCl4], 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. |
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| Keywords: | allylboron borenium borocation carboboration main group |
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