Efficient Pd-catalyzed coupling of tautomerizable heterocycles with terminal alkynes via C-OH bond activation using PyBrOP

Ce Shi; Courtney C. Aldrich

doi:10.1021/ol100657n

Efficient Pd-catalyzed coupling of tautomerizable heterocycles with terminal alkynes via C-OH bond activation using PyBrOP

Ce Shi
, Courtney C. Aldrich

Medicinal Chemistry

Research output: Contribution to journal › Article › peer-review

53 Scopus citations

Abstract

The direct alkynylation of tautomerizable heterocylcles is described via a two-step process involving in situ C-OH activation with bromotripyrrolidinophosphonium hexafluorophosphate (PyBrOP) followed by Sonogashira coupling with a wide range of alkyl or aryl terminal alkynes using a copper-free system employing PdCl₂(CH₃CN)₂ and 2-(dicyclohexylphosphino)biphenyl.

Original language	English (US)
Pages (from-to)	2286-2289
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	10
DOIs	https://doi.org/10.1021/ol100657n
State	Published - May 21 2010

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10.1021/ol100657n

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abstract = "The direct alkynylation of tautomerizable heterocylcles is described via a two-step process involving in situ C-OH activation with bromotripyrrolidinophosphonium hexafluorophosphate (PyBrOP) followed by Sonogashira coupling with a wide range of alkyl or aryl terminal alkynes using a copper-free system employing PdCl2(CH3CN)2 and 2-(dicyclohexylphosphino)biphenyl.",

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journal = "Organic Letters",

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AU - Aldrich, Courtney C.

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N2 - The direct alkynylation of tautomerizable heterocylcles is described via a two-step process involving in situ C-OH activation with bromotripyrrolidinophosphonium hexafluorophosphate (PyBrOP) followed by Sonogashira coupling with a wide range of alkyl or aryl terminal alkynes using a copper-free system employing PdCl2(CH3CN)2 and 2-(dicyclohexylphosphino)biphenyl.

AB - The direct alkynylation of tautomerizable heterocylcles is described via a two-step process involving in situ C-OH activation with bromotripyrrolidinophosphonium hexafluorophosphate (PyBrOP) followed by Sonogashira coupling with a wide range of alkyl or aryl terminal alkynes using a copper-free system employing PdCl2(CH3CN)2 and 2-(dicyclohexylphosphino)biphenyl.

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UR - https://www.scopus.com/pages/publications/77952369092#tab=citedBy

U2 - 10.1021/ol100657n

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JO - Organic Letters

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ER -

Efficient Pd-catalyzed coupling of tautomerizable heterocycles with terminal alkynes via C-OH bond activation using PyBrOP

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