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Issue 39, 2020

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

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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


Submitted
06 Mar 2020
Accepted
21 May 2020
First published
27 May 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 10770-10777
Article type
Edge Article

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.

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