Photoinduced Divergent Deaminative Borylation and Hydrodeamination of Primary Aromatic Amines

We have developed the divergent deaminative borylation and hydrodeamination of primary aromatic amines using bis­(pinacolato)­diboron. These transformations can be switched by the reaction conditions. Mechanistic and computational studies have suggested that the cleavage of the C–N bond and the form...

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Published inOrganic letters Vol. 24; no. 23; pp. 4281 - 4285
Main Authors Shiozuka, Akira, Sekine, Kohei, Toki, Takumi, Kawashima, Kyohei, Mori, Toshifumi, Kuninobu, Yoichiro
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.06.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PATHWAYS
OLEFINS
CLEAVAGE
ARYLAMINES
CARBON-NITROGEN BOND
ARYLATION
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Summary:We have developed the divergent deaminative borylation and hydrodeamination of primary aromatic amines using bis­(pinacolato)­diboron. These transformations can be switched by the reaction conditions. Mechanistic and computational studies have suggested that the cleavage of the C–N bond and the formation of C–B bond are unlikely to involve free aryl radical intermediates. However, hydrodeamination is shown to proceed via hydrogen atom transfer between the corresponding aryl radical and an ethereal solvent.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01663