Microwave-assisted C-C Bond Formation of Diarylacetylenes and Aromatic Hydrocarbons on Carbon Beads Under Continuous-flow Conditions

Overview

Journal Commun Chem

Publisher Springer Nature

Specialty Chemistry

Date 2023 Apr 24

PMID 37095153

Authors

Tsuyoshi Yamada

Wataru Teranishi

Naoya Sakurada

Seiya Ootori

Yuka Abe

Tomohiro Matsuo

Yasuharu Morii

Masatoshi Yoshimura

Takeo Yoshimura

Takashi Ikawa

Hironao Sajiki

Affiliations

Soon will be listed here.

Abstract

The synthesis of polycyclic aromatic compounds generally requires stoichiometric oxidants or homogeneous metal catalysts, however, the risk of contamination of inorganic residues can affect their properties. Here we present a microwave (MW)-assisted platinum on beaded activated carbon (Pt/CB)-catalyzed C-C bond formation of diarylacetylenes and aromatic hydrocarbons under continuous-flow conditions. Various fused aromatic compounds were continuously synthesized via dehydrogenative C(sp)-C(sp) and C(sp)-C(sp) bond formation with yields of up to 87% without the use of oxidants and bases. An activated, local reaction site on Pt/CB in the flow reaction channel reaching temperatures of more than three hundred degrees Celsius was generated in the catalyst cartridge by selective microwave absorption in CB with an absorption efficiency of > 90%. Mechanistic experiments of the transformation reaction indicated that a constant hydrogen gas supply was essential for activating Pt. This is an ideal reaction with minimal input energy and no waste production.

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