The propargyl rearrangement to functionalised allyl-boron and borocation compounds
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...
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| Main Authors: | , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
26 September 2016
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| In: |
Chemistry - a European journal
Year: 2016, Volume: 22, Issue: 41, Pages: 14618-14624 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201602719 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1002/chem.201602719 Verlag, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/chem.201602719/abstract 
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| Author Notes: | Lewis C. Wilkins, James R. Lawson, Philipp Wieneke, Frank Rominger, A. Stephen K. Hashmi, Max M. Hansmann, and Rebecca L. Melen |
| Summary: | 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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| Item Description: | Gesehen am 25.08.2017 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201602719 |