Selective synthesis of N-unsubstituted and N-arylindoles by the reaction of arynes with azirines
| Title | Selective synthesis of N-unsubstituted and N-arylindoles by the reaction of arynes with azirines |
| Publication Type | Journal Article |
| Year of Publication | 2016 |
| Authors | Thangaraj, M, Bhojgude, SSuresh, Jain, S"", Gonnade, RG, Biju, AT |
| Journal | Journal of Organic Chemistry |
| Volume | 81 |
| Issue | 18 |
| Pagination | 8604-8611 |
| Date Published | SEP |
| Abstract | The transition-metal-free and temperature-dependent highly selective reaction of arynes with 2H-azirines allowing the synthesis of either N-unsubstituted or N-arylindoles has been developed. At 60 degrees C, arynes generated from 2-(trimethylsilyl)aryl triflates smoothly insert into 2H-azirines to form 2,3-diarylindoles with high selectivity. Interestingly, when the reaction was performed at -10 degrees C, the selectivity was switched to the formation of 1,2,3-triarylindoles in good yields. |
| DOI | 10.1021/acs.joc.6b01472 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 4.785 |
Divison category:
Center for Material Characterization (CMC)
Organic Chemistry
Physical and Materials Chemistry