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

Karl J. Hale | Zendy; Ziyue Xiong | Zendy; Liping Wang | Zendy; Soraya Manaviazar | Zendy; Ryan Mackle | Zendy

Open Access

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

Author(s) -

Karl J. Hale,

Ziyue Xiong,

Liping Wang,

Soraya Manaviazar,

Ryan Mackle

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol503222j

Subject(s) - paraformaldehyde , chemistry , terminal (telecommunication) , metalation , base (topology) , stoichiometry , combinatorial chemistry , protocol (science) , alkynylation , medicinal chemistry , stereochemistry , organic chemistry , catalysis , computer network , computer science , medicine , mathematical analysis , alternative medicine , mathematics , pathology

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 °C. Significantly, the method can be successfully applied on acetylenes that possess base-sensitive ester functionality and heterocyclic rings that readily undergo metalation. While N-methylephedrine (NME) is generally the best Zn(OTf)2-coordinating ligand for promoting hydroxymethylation, TMEDA can serve as a replacement.

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