Lewis acid–base 1,2-addition reactions: synthesis of pyrylium borates from en-ynoate precursors

Lewis C. Wilkins; Hugh B. Hamilton; Benson M. Kariuki; A. Stephen K. Hashmi; Max M. Hansmann; Rebecca L. Melen

doi:10.1039/C5DT03340C

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Lewis acid–base 1,2-addition reactions: synthesis of pyrylium borates from en-ynoate precursors†

Lewis C. Wilkins,^a Hugh B. Hamilton,^a Benson M. Kariuki,^a A. Stephen K. Hashmi,^bc Max M. Hansmann^b and Rebecca L. Melen*^a

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* Corresponding authors

^a School of Chemistry, Main Building, Cardiff University, Cardiff CF10 3AT, Cymru/Wales, UK
E-mail: melenr@cardiff.ac.uk
Tel: +(44) 2920 879667

^b Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany

^c Chemistry Department, Faculty of Science, King Abdulaziz University (KAU), Jeddah 21589, Saudi Arabia

Abstract

Treatment of methyl (Z)-2-alken-4-ynoates with the strong Lewis acid tris(pentafluorophenyl) borane, B(C₆F₅)₃, yield substituted zwitterionic pyrylium borate species via an intramolecular 6-endo-dig cyclisation reaction.

This article is part of the themed collection: Main Group Transformations

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DOI: https://doi.org/10.1039/C5DT03340C
Article type: Communication
Submitted: 28 Aug 2015
Accepted: 22 Sep 2015
First published: 25 Sep 2015
This article is Open Access

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Dalton Trans., 2016,45, 5929-5932

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Lewis acid–base 1,2-addition reactions: synthesis of pyrylium borates from en-ynoate precursors

L. C. Wilkins, H. B. Hamilton, B. M. Kariuki, A. S. K. Hashmi, M. M. Hansmann and R. L. Melen, Dalton Trans., 2016, 45, 5929 DOI: 10.1039/C5DT03340C

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Dalton Transactions

Lewis acid–base 1,2-addition reactions: synthesis of pyrylium borates from en-ynoate precursors†

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Lewis acid–base 1,2-addition reactions: synthesis of pyrylium borates from en-ynoate precursors

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