Bismuth(III)-catalyzed cycloisomerization and (hetero)arylation of alkynols: simple access to 2-(hetero)aryl tetrahydrofurans and tetrahydropyrans
| Title | Bismuth(III)-catalyzed cycloisomerization and (hetero)arylation of alkynols: simple access to 2-(hetero)aryl tetrahydrofurans and tetrahydropyrans |
| Publication Type | Journal Article |
| Year of Publication | 2018 |
| Authors | Nakate, AK, Pratapure, MS, Kontham, R |
| Journal | Organic & Biomolecular Chemistry |
| Volume | 16 |
| Issue | 17 |
| Pagination | 3229-3240 |
| Date Published | MAY |
| Abstract | 2-(Hetero)aryl tetrahydrofurans and tetrahydropyrans were successfully synthesized using Bi(OTf)(3)-catalyzed hydroalkoxylation (cycloisomerization) of alkynols (via 5 or 6 exo-dig cyclization) and intermolecular (hetero)arylation. This reaction involves a highly efficient cascade process, where initially the alkynol undergoes a cycloisomerization step via activation of the triple bond and generates the oxocarbenium ion, which subsequently participates in the (hetero)hydroarylation step with electron-rich arenes. Simple to complex suitably functionalized alkynols (4-pentyn-1-ols and 5-hexyn-1-ols) and electron-rich aromatic compounds were found to be reliable substrates in this cascade transformation and furnished a wide range of oxygen heterocycles. This practical tandem process provides a means to build libraries related to pharmacologically active molecules and natural product like scaffolds. |
| DOI | 10.1039/c8ob00368h |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.564 |
Divison category:
Organic Chemistry