Photoinduced Deaminative Borylation of Unreactive Aromatic Amines Enhanced by CO2

Akira Shiozuka; Kohei Sekine; Yoichiro Kuninobu

doi:10.1021/acs.orglett.1c01503

Photoinduced Deaminative Borylation of Unreactive Aromatic Amines Enhanced by CO₂

Akira Shiozuka, Kohei Sekine, Yoichiro Kuninobu

Department of Fundamental Organic Chemistry

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

Abstract

Herein, direct unreactive C-N borylation of aromatic amines by a photocatalyst was achieved. The C-N borylation of aromatic amines with bis(pinacolato)diboron (B2pin2) proceeded using a pyrene catalyst under light irradiation to afford desired borylated products and aminoborane as a byproduct. The yield of the borylated product improved under a CO2 atmosphere which probably reduced the inhibitory effect of aminoborane. Mechanistic studies suggested that the C-N bond cleavage and C-B bond formation proceeded via a concerted pathway.

Original language	English
Pages (from-to)	4774-4778
Number of pages	5
Journal	Organic letters
Volume	23
Issue number	12
DOIs	https://doi.org/10.1021/acs.orglett.1c01503
Publication status	Published - Jun 18 2021

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Photoinduced Deaminative Borylation of Unreactive Aromatic Amines Enhanced by CO2",

abstract = "Herein, direct unreactive C-N borylation of aromatic amines by a photocatalyst was achieved. The C-N borylation of aromatic amines with bis(pinacolato)diboron (B2pin2) proceeded using a pyrene catalyst under light irradiation to afford desired borylated products and aminoborane as a byproduct. The yield of the borylated product improved under a CO2 atmosphere which probably reduced the inhibitory effect of aminoborane. Mechanistic studies suggested that the C-N bond cleavage and C-B bond formation proceeded via a concerted pathway.",

author = "Akira Shiozuka and Kohei Sekine and Yoichiro Kuninobu",

note = "Funding Information: This work was supported in part by JSPS KAKENHI Grant Numbers JP 17H03016, 18H04656, and 20H04824, Takeda Science Foundation, The Mitsubishi Foundation, and Yamada Science Foundation. This work was the result of using research equipment shared in the MEXT Project for promoting public utilization of the advanced research infrastructure (program for supporting introduction of the new sharing system) Grant Number JPMXS0422300120. Publisher Copyright: {\textcopyright} ",

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T1 - Photoinduced Deaminative Borylation of Unreactive Aromatic Amines Enhanced by CO2

AU - Shiozuka, Akira

AU - Sekine, Kohei

AU - Kuninobu, Yoichiro

N1 - Funding Information: This work was supported in part by JSPS KAKENHI Grant Numbers JP 17H03016, 18H04656, and 20H04824, Takeda Science Foundation, The Mitsubishi Foundation, and Yamada Science Foundation. This work was the result of using research equipment shared in the MEXT Project for promoting public utilization of the advanced research infrastructure (program for supporting introduction of the new sharing system) Grant Number JPMXS0422300120. Publisher Copyright: ©

PY - 2021/6/18

Y1 - 2021/6/18

N2 - Herein, direct unreactive C-N borylation of aromatic amines by a photocatalyst was achieved. The C-N borylation of aromatic amines with bis(pinacolato)diboron (B2pin2) proceeded using a pyrene catalyst under light irradiation to afford desired borylated products and aminoborane as a byproduct. The yield of the borylated product improved under a CO2 atmosphere which probably reduced the inhibitory effect of aminoborane. Mechanistic studies suggested that the C-N bond cleavage and C-B bond formation proceeded via a concerted pathway.

AB - Herein, direct unreactive C-N borylation of aromatic amines by a photocatalyst was achieved. The C-N borylation of aromatic amines with bis(pinacolato)diboron (B2pin2) proceeded using a pyrene catalyst under light irradiation to afford desired borylated products and aminoborane as a byproduct. The yield of the borylated product improved under a CO2 atmosphere which probably reduced the inhibitory effect of aminoborane. Mechanistic studies suggested that the C-N bond cleavage and C-B bond formation proceeded via a concerted pathway.

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Photoinduced Deaminative Borylation of Unreactive Aromatic Amines Enhanced by CO₂

Abstract

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