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Photoinduced Deaminative Borylation of Unactivated Aromatic Amines Enhanced by CO2

preprint
submitted on 10.04.2021, 07:08 and posted on 12.04.2021, 13:04 by Akira Shiozuka, Kohei Sekine, Yoichiro Kuninobu
Herein, direct unactivated C-N borylation of aromatic amines by a photocatalyst was achieved under mild and metal-free conditions. The C-N borylation of aromatic amines with bis(pinacolato)diboron (B2pin2) proceeded in the presence of a pyrene catalyst under light irradiation (λ = 365 nm) to afford desired borylated products and aminoborane as a byproduct. The yield of borylated product improved under a CO2 atmosphere. Reactions conducted in the presence of a stoichiometric amount of aminoborane under N2 or CO2 indicated that CO2 reduced the inhibitory effect of aminoborane. Optimal reaction conditions were applied to a variety of aromatic amines. Mechanistic studies suggested that the C-N bond cleavage and C-B bond formation proceeded via a concerted pathway.

Funding

JSPS KAKENHI JP 17H03016

JSPS KAKENHI JP 18H04656

JSPS KAKENHI JP 20H04824

Takeda Science Foundation

Mitsubishi Foundation

Yamada Science Foundation

History

Email Address of Submitting Author

kuninobu@cm.kyushu-u.ac.jp

Institution

Kyushu University

Country

Japan

ORCID For Submitting Author

0000-0002-8679-9487

Declaration of Conflict of Interest

The authors declare no competing financial interest.

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