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Synthesis 2022; 54(22): 5119-5127
DOI: 10.1055/s-0041-1737342
DOI: 10.1055/s-0041-1737342
paper
Formation of a Naphthalene Framework by Rhodium(III)-Catalyzed Double C–H Functionalization of Arenes with Alkynes: Impact of a Supporting Ligand and an Acid Additive
The main synthetic work was supported by the Russian Science Foundation (grant # 17-73-30036).
Abstract
An efficient protocol has been developed for the synthesis of larger condensed arenes from aromatic hydrocarbons and internal alkynes. This protocol uses readily available [CpRhI2]n as a catalyst and Cu(OAc)2 as an oxidant and proceeds smoothly through undirected double C–H activation. The addition of trifluoroacetic acid has a crucial positive impact on the reaction selectivity and the yields of the target products. In contrast to the previously reported catalytic systems, the new conditions allow the use of both dialkyl- and diarylacetylenes with the same high efficiency.
Key words
acenes - C–H activation - homologation - non-chelate-assisted C–H functionalization - rhodium catalysisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737342.
- Supporting Information
Publication History
Received: 08 November 2021
Accepted after revision: 14 December 2021
Article published online:
15 February 2022
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For representative works, see:
For selected reviews, see:
For Pd-catalyzed annulations, see:
For Rh-catalyzed annulations, see:
For Ir-catalyzed annulations, see:
For example, see: