Synthesis of 1,3-Dialkylimidazol-2-ylidene Boranes from 1,3-Dialkylimidazolium Iodides and Sodium Borohydride

The Journal of Organic Chemistry
Sean GardnerDennis P Curran

Abstract

1,3-Dialkylimidazol-2-ylidene boranes have been made in moderate yields (typically 23-53%) from the corresponding N-alkyl imidazole, an alkylating agent (usually MeI), and sodium borohydride (NaBH4). The two-step, one-pot reaction sequence takes about 1 day to perform. The reagents are inexpensive, and the reactions are easy to conduct. The synthesis of 1,3-dimethylimidazol-2-ylidene borane has been conducted on scales up to 100 mmol and is especially convenient because the pure product can be isolated by direct recrystallization from water.

References

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Jan 29, 2010·Journal of the American Chemical Society·John C WaltonDennis P Curran
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Dec 14, 2011·Organic Letters·Markus HornDennis P Curran
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Oct 28, 2014·Angewandte Chemie·Tsuyoshi Taniguchi, Dennis P Curran

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Citations

May 26, 2017·Organic Letters·Vyacheslav I SupranovichAlexander D Dilman
Apr 13, 2018·Physical Chemistry Chemical Physics : PCCP·Steffen Tröger-MüllerClemens Liedel
Jun 22, 2018·Angewandte Chemie·Daniel SubervieEmmanuel Lacôte
Jun 19, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Jannick GuschlbauerJörg Sundermeyer
Jun 22, 2019·Angewandte Chemie·Simon RohrbachJohn A Murphy
May 5, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·N BridonneauF Ribot
May 10, 2017·Chemistry : a European Journal·John S McGoughMichael J Ingleson
Jan 23, 2021·Organic Letters·Kosuke TakahashiTsuyoshi Taniguchi
Jul 13, 2021·Chemical Society Reviews·Tsuyoshi Taniguchi
Feb 27, 2020·Journal of the American Chemical Society·Wen DaiDennis P Curran
Nov 9, 2017·The Journal of Organic Chemistry·Daniel A Bolt, Dennis P Curran
Nov 10, 2017·The Journal of Organic Chemistry·Takashi WatanabeTsuyoshi Taniguchi

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