TY - JOUR
T1 - Construction of 1,2,3-Benzodiazaborole by Electrophilic Borylation of Azobenzene and Nucleophilic Dialkylative Cyclization
AU - Shigeno, Masanori
AU - Imamatsu, Masaya
AU - Kai, Yusuke
AU - Kiriyama, Moe
AU - Ishida, Shintaro
AU - Nozawa-Kumada, Kanako
AU - Kondo, Yoshinori
N1 - Funding Information:
This work was financially supported by JSPS KAKENHI grant number 19H03346 (Y.Kondo), JSPS KAKENHI grant number 19K06967 (M.S.), the Environment Research and Technology Development Fund (JPMEERF20202R02) of the Environmental Restoration and Conservation Agency of Japan (M.S.), The Uehara Memorial Foundation (M.S.), The Tokyo Biochemical Research Foundation (M.S.), The Research Foundation for Pharmaceutical Sciences (M.S.), the Daicel Corporation (M.S.), and also the Platform Project for Supporting Drug Discovery and Life Science Research funded by Japan Agency for Medical Research and Development (AMED) (M.S., K.N.-K., and Y.Kondo).
Publisher Copyright:
© 2021 American Chemical Society.
PY - 2021/10/15
Y1 - 2021/10/15
N2 - 1,2,3-Benzodiazaboroles can be conveniently prepared from azobenzenes by a two-step protocol involving electrophilic ortho-borylation with BBr3 and dialkylative cyclization with the Grignard reagent. The methodology provides a diverse range of products equipped with functionalities from azobenzenes containing substituents (Me, t-Bu, F, Cl, Br, I, and OCF3) and a series of Grignard reagents (alkyl- and arylmagnesium reagents). Moreover, this study displays the moderate aromaticity of the B-N-N-containing five-membered ring and mechanistic investigations of the cyclization reaction.
AB - 1,2,3-Benzodiazaboroles can be conveniently prepared from azobenzenes by a two-step protocol involving electrophilic ortho-borylation with BBr3 and dialkylative cyclization with the Grignard reagent. The methodology provides a diverse range of products equipped with functionalities from azobenzenes containing substituents (Me, t-Bu, F, Cl, Br, I, and OCF3) and a series of Grignard reagents (alkyl- and arylmagnesium reagents). Moreover, this study displays the moderate aromaticity of the B-N-N-containing five-membered ring and mechanistic investigations of the cyclization reaction.
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U2 - 10.1021/acs.orglett.1c03033
DO - 10.1021/acs.orglett.1c03033
M3 - Article
C2 - 34613748
AN - SCOPUS:85117450367
SN - 1523-7060
VL - 23
SP - 8023
EP - 8027
JO - Organic Letters
JF - Organic Letters
IS - 20
ER -