Carreira alkynylations with paraformaldehyde. a mild and convenient protocol for the hydroxymethylation of complex base-sensitive terminal acetylenes via alkynylzinc triflates
Hale, KJ; Xiong, Z; Wang, L; Manaviazar, S; Mackle, R
| HERO ID | 2993745 |
|---|---|
| In Press | No |
| Year | 2015 |
| Title | Carreira alkynylations with paraformaldehyde. a mild and convenient protocol for the hydroxymethylation of complex base-sensitive terminal acetylenes via alkynylzinc triflates |
| Authors | Hale, KJ; Xiong, Z; Wang, L; Manaviazar, S; Mackle, R |
| Journal | Organic Letters |
| Volume | 17 |
| Issue | 2 |
| Page Numbers | 198-201 |
| 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 °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. |
| Doi | 10.1021/ol503222j |
| Pmid | 25539470 |
| Wosid | WOS:000348331800008 |
| Url | http://dx.doi.org/10.1021%2Fol503222j Available from publisher's site |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |
| Keyword | alkynes; chemical reactions; chemical structure; formaldehyde; ligands; Internet resource |