Carreira Alkynylations with Paraformaldehyde. A Mild and Convenient Protocol for the Hydroxymethylation of Complex Base-SensitiveTerminal Acetylenes via Alkynylzinc Triflates

Karl J. Hale, Ziyue Xiong, Liping Wang, Soraya Manaviazar, Ryan Mackle

Research output: Contribution to journalArticle

9 Citations (Scopus)
262 Downloads (Pure)

Abstract

A new synthetic protocol for the hydroxymethylation of terminal acetylenes is described that involves stoichiometric Carreira alkynylation with solid paraformaldehyde (HO[CH2O]nH) in PhMe at 60 oC. Significantly, the method can be successfully applied on acetylenes that possess base-sensitive ester functionality and heterocyclic rings that readily undergo metallation. While N-methylephedrine (NME) is generally the best Zn(OTf)2-coordinating ligand for promoting hydroxymethylation, TMEDA can serve as a replacement.
Original languageEnglish
Pages (from-to)198-201
Number of pages4
JournalOrganic Letters
Volume17
Issue number2
Early online date24 Dec 2014
DOIs
Publication statusPublished - 16 Jan 2015

Keywords

  • Alkyne Hydroxymethylation with Paraformaldehyde
  • Carreira Alkynylation
  • Hale O-Directed Alkyne Free Radical Hydrostannation

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Carreira Alkynylations with Paraformaldehyde. A Mild and Convenient Protocol for the Hydroxymethylation of Complex Base-SensitiveTerminal Acetylenes via Alkynylzinc Triflates'. Together they form a unique fingerprint.

Cite this