Cyclization of carbonyl groups onto alkynes upon reaction with IPy2BF4 and their trapping with nucleophiles: a versatile trigger for assembling oxygen heterocycles

Journal of the American Chemical Society
José BarluengaJosé M González

Abstract

Iodonium ions liberated from bis(pyridine)iodonium(I) tetrafluoroborate react with ortho-alkynyl-substituted carbonyl compounds and different nucleophiles to give valuable iodinated heterocycles at room temperature, through a new and metal-free reaction sequence. Interestingly, the nature of the nucleophile can be widely modified, and not only alcohols but also several carbon-based nucleophiles can be nicely used.

References

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Citations

Jul 29, 2011·ACS Combinatorial Science·Trapti AggarwalAkhilesh K Verma
Apr 19, 2005·Chemical Communications : Chem Comm·José BarluengaJosé M González
Jul 13, 2005·Chemical Communications : Chem Comm·Yewen Fang, Chaozhong Li
May 8, 2010·Chemical Communications : Chem Comm·Yoshinori YamamotoTienan Jin
Sep 3, 2009·Chemical Communications : Chem Comm·Yong-Xin XieYong-Min Liang
Feb 22, 2011·Chemical Communications : Chem Comm·Fan YangYoshinori Yamamoto
Aug 2, 2011·Beilstein Journal of Organic Chemistry·Sara Hummel, Stefan F Kirsch
Oct 27, 2015·The Journal of Organic Chemistry·Maciej E DomaradzkiYu Chen
Jun 7, 2016·Journal of the American Chemical Society·Anna-Carin C CarlssonMáté Erdélyi
Nov 3, 2006·Organic Letters·Naoki Asao, Kenichiro Sato
Nov 5, 2005·Organic Letters·Jesse P Waldo, Richard C Larock
Feb 10, 2018·Angewandte Chemie·Yuk-Cheung Chan, Ying-Yeung Yeung
Mar 25, 2011·Chemistry : a European Journal·Fang YangYong-Min Liang
Dec 31, 2008·Angewandte Chemie·Akhilesh Kumar VermaRichard C Larock
Jun 24, 2005·Chemistry : a European Journal·Francisco J FañanásFélix Rodríguez
May 19, 2010·Angewandte Chemie·Benedikt CroneKlaus-Daniel Umland
Nov 26, 2009·Chemistry : a European Journal·Jan P WeyrauchJan W Bats
May 11, 2019·Angewandte Chemie·Alan VanderkooyMáté Erdélyi
Mar 27, 2020·Chemical Society Reviews·Lotta Turunen, Máté Erdélyi
Jun 6, 2015·Chemistry : a European Journal·Rohan VolpeBernard L Flynn

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