Publication Details:
Title: Double annulation of ortho- and peri-C–H bonds of fused (hetero)arenes to unusual oxepino-pyridines
| Author(s) | Majji Shankar, Raja K. Rit, Somratan Sau,Kallol Mukherjee,a Vincent Gandon * and Akhila K. Sahoo* : Chem. Sci., 2020, 11, 10770-10777 |
|---|---|
| Journal Name | Chemical Science |
| Link to | https://pubs.rsc.org/en/content/articlelanding/2020/sc/d0sc01373k#!divAbstract |
| journal image URL | http://chemistry.uohyd.ac.in/~aks/wp-content/uploads/chemicalSc.jpg |
More Details:
Direct difunctionalization of chemically distinct ortho– and peri-C–H bonds of fused hetero(arenes) is illustrated through an unusual one-pot domino {[4 + 2] & [5 + 2]} double annulation with alkynes for the first time. This process is viable under Ru(II)-catalysis using a sulfoximine directing group and builds four bonds [(C–C)–(C–N) and (C–C)–(C–O)] in a single operation. Such synthetic manifestation offers access to uncommon [6,7]-fused oxepino-pyridine skeletons. DFT calculations provide mechanistic insight into this double annulation of naphthoic acid derivatives with alkynes and corroborate the participation of a ruthena-oxabicyclooctene intermediate, which is responsible for the rare 7-membered ring formation.