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2023•Organic LettersOpen access

Copper-Catalyzed Borylation of Styrenes by 1,8-Diaminonaphthalene-Protected Diboronic Acid

Taiga Yasuda, Yusuke Yoshigoe, Shinichi Saito

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Abstract

High Resolution Image Download MS PowerPoint Slide We report a concise synthesis of 1,8-diaminonaphthalene-protected diboronic acid (B 2 (dan) 2 ), which is a promising borylating agent. B 2 (dan) 2 is a bench-stable compound, and it could be utilized for Cu-catalyzed borylation of styrene derivatives. The reaction proceeded in a highly selective manner, and the products were isolated in up to 97% yields. Mechanistic studies revealed that a borate species would be a key intermediate for the borylation reaction.

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High Resolution Image Download MS PowerPoint Slide We report a concise synthesis of 1,8-diaminonaphthalene-protected diboronic acid (B 2 (dan) 2 ), which is a promising borylating agent. B 2 (dan) 2 is a bench-stable compound, and it could be utilized for Cu-catalyzed borylation of styrene derivatives. The reaction proceeded in a highly selective manner, and the products were isolated in up to 97% yields. Mechanistic studies revealed that a borate species would be a key intermediate for the borylation reaction.

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Available abstract

High Resolution Image Download MS PowerPoint Slide We report a concise synthesis of 1,8-diaminonaphthalene-protected diboronic acid (B 2 (dan) 2 ), which is a promising borylating agent. B 2 (dan) 2 is a bench-stable compound, and it could be utilized for Cu-catalyzed borylation of styrene derivatives. The reaction proceeded in a highly selective manner, and the products were isolated in up to 97% yields. Mechanistic studies revealed that a borate species would be a key intermediate for the borylation reaction.

Key concepts: Borylation, Chemistry, Catalysis, Boron, Styrene, Organoboron compounds, Combinatorial chemistry, Organic chemistry

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