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月 2020
Accepted
21 5月 2020
First published
27 5月 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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements