Fluoride-mediated dephosphonylation of alpha-diazo-beta-carbonyl phosphonates
| Title | Fluoride-mediated dephosphonylation of alpha-diazo-beta-carbonyl phosphonates |
| Publication Type | Journal Article |
| Year of Publication | 2017 |
| Authors | Phatake, RS, Mullapudi, V, Wakchaure, VC, Ramana, CV |
| Journal | Organic Letters |
| Volume | 19 |
| Issue | 2 |
| Pagination | 372-375 |
| Date Published | JAN |
| Abstract | The possibility of fluoride-mediated selective dephosphonylation of alpha-diazo-beta-carbonyl phosphonates such as the Ohira-Bestmann reagent has been proposed and executed. The resulting alpha-diazocarbonyl intermediates undergo a (3 + 2)pcycloaddition at room temperature with conjugated olefins and benzynes. Interestingly, under the current conditions, the resulting cycloaddition products underwent either N-acylation (with excess alpha-diazo-beta-carbonyl phosphonates) or Michael addition (with conjugated olefins). |
| DOI | 10.1021/acs.orglett.6b03573 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 6.732 |
Divison category:
Organic Chemistry