Carreira Alkynylations with Paraformaldehyde. A Mild and Convenient Protocol for the Hydroxymethylation of Complex Base-SensitiveTerminal Acetylenes via Alkynylzinc Triflates
| Data(s) |
16/01/2015
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| Resumo |
A new synthetic protocol for the hydroxymethylation of terminal acetylenes is described that involves <i>stoichiometric</i> Carreira alkynylation with solid paraformaldehyde (HO[CH<sub>2</sub>O]<sub>n</sub>H) in PhMe at 60 <sup>o</sup>C. Significantly, the method can be successfully applied on acetylenes that possess base-sensitive ester functionality and heterocyclic rings that readily undergo metallation. While <i>N</i>-methylephedrine (NME) is generally the best Zn(OTf)<sub>2</sub>-coordinating ligand for promoting hydroxymethylation, TMEDA can serve as a replacement. |
| Formato |
application/vnd.openxmlformats-officedocument.wordprocessingml.document |
| Identificador |
http://dx.doi.org/10.1021/ol503222j http://pure.qub.ac.uk/ws/files/13793298/Hale_Final_Version_Proof_Deletions.docx |
| Idioma(s) |
eng |
| Direitos |
info:eu-repo/semantics/openAccess |
| Fonte |
Hale , K J , Xiong , Z , Wang , L , Manaviazar , S & Mackle , R 2015 , ' Carreira Alkynylations with Paraformaldehyde. A Mild and Convenient Protocol for the Hydroxymethylation of Complex Base-SensitiveTerminal Acetylenes via Alkynylzinc Triflates ' Organic Letters , vol 17 , no. 2 , pp. 198-201 . DOI: 10.1021/ol503222j |
| Palavras-Chave | #Alkyne Hydroxymethylation with Paraformaldehyde #Carreira Alkynylation #Hale O-Directed Alkyne Free Radical Hydrostannation #/dk/atira/pure/subjectarea/asjc/1600 #Chemistry(all) |
| Tipo |
article |
