4.7 Article

Unveiling the uncatalyzed reaction of alkynes with 1,2-dipoles for the room temperature synthesis of cyclobutenes

期刊

CHEMICAL COMMUNICATIONS
卷 51, 期 16, 页码 3395-3398

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/c4cc10111a

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  1. MINECO
  2. FEDER [CTQ2012-33664-C02-01, CTQ2012-33664-C02-02, CTQ2013-44303-P]
  3. UCM

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2-(Pyridinium-1-yl)-1,1-bis(triflyl)ethanides have been used as 1,2-dipole precursors in a metal-free direct [2+2] cycloaddition reaction of alkynes. Starting from stable zwitterionic pyridinium salts, the electron deficient olefin 1,1-bis(trifluoromethylsulfonyl)ethene is generated in situ and immediately reacted at room temperature with an alkyne to afford substituted cyclobutenes. Remarkably, this mild and facile uncatalyzed protocol requires neither irradiation nor heating.

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