Issue 39, 2020

Double annulation of ortho- and peri-C–H bonds of fused (hetero)arenes to unusual oxepino-pyridines

Abstract

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.

Graphical abstract: Double annulation of ortho- and peri-C–H bonds of fused (hetero)arenes to unusual oxepino-pyridines

Supplementary files

Article information

Article type
Edge Article
Submitted
06 3 2020
Accepted
21 5 2020
First published
27 5 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2020,11, 10770-10777

Double annulation of ortho- and peri-C–H bonds of fused (hetero)arenes to unusual oxepino-pyridines

M. Shankar, R. K. Rit, S. Sau, K. Mukherjee, V. Gandon and A. K. Sahoo, Chem. Sci., 2020, 11, 10770 DOI: 10.1039/D0SC01373K

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