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

Vladimir B. Kharitonov; Dmitry V. Muratov; Yulia V. Nelyubina; Dmitry A. Loginov

doi:10.1055/s-0041-1737342

Synthesis, Table of Contents

Synthesis 2022; 54(22): 5119-5127
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

Vladimir B. Kharitonov

^aA. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, 119991 Moscow, Russian Federation

^bDmitry Mendeleev University of Chemical Technology of Russia, Miusskaya sq. 9, Moscow 125047, Russian Federation

,

Dmitry V. Muratov

^aA. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, 119991 Moscow, Russian Federation

,

Yulia V. Nelyubina

^aA. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, 119991 Moscow, Russian Federation

,

Dmitry A. Loginov ∗

^aA. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, 119991 Moscow, Russian Federation

^cG. V. Plekhanov Russian University of Economics, 36 Stremyanny Per., Moscow 117997, Russian Federation

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Abstract

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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 catalysis

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