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Synlett
DOI: 10.1055/a-2315-8369
letter

Silver-mediated homocoupling of arylboronic acids

Tomoya Sakaguchi
1   Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology, Osaka, Japan (Ringgold ID: RIN57935)
,
Kyuta Fukuoka
1   Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology, Osaka, Japan (Ringgold ID: RIN57935)
,
Takuya Matsuki
1   Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology, Osaka, Japan (Ringgold ID: RIN57935)
,
Misa Kawase
1   Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology, Osaka, Japan (Ringgold ID: RIN57935)
,
Aya Tazawa
2   Complex Catalysis, Institute for Molecular Science, Okazaki, Japan (Ringgold ID: RIN88301)
,
Yasuhiro Uozumi
2   Complex Catalysis, Institute for Molecular Science, Okazaki, Japan (Ringgold ID: RIN88301)
,
Yoshimasa Matsumura
1   Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology, Osaka, Japan (Ringgold ID: RIN57935)
,
Osamu Shimomura
1   Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology, Osaka, Japan (Ringgold ID: RIN57935)
,
Atsushi Ohtaka 
3   Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology, Osaka, Japan (Ringgold ID: RIN57935)
› Author AffiliationsSupported by: Japan Society for the Promotion of Science #22K05201
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Here we describe a homocoupling reaction of arylboronic acid facilitated by silver carbonate, which proceeds smoothly in MeOH even at ambient temperature. The reaction exhibits broad functional group compatibility, affording a variety of symmetrical biaryls in satisfactory yields. Silver nanoparticles formed in situ serve as an accelerator in this process. Moreover, initial mechanistic investigations suggest that this transformation may occur via a radical mechanism.



Publication History

Received: 12 April 2024

Accepted after revision: 27 April 2024

Accepted Manuscript online:
27 April 2024

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