TY - JOUR
T1 - Organic superbase t-Bu-P4-catalyzed demethylations of methoxyarenes
AU - Shigeno, Masanori
AU - Hayashi, Kazutoshi
AU - Korenaga, Toshinobu
AU - Nozawa-Kumada, Kanako
AU - Kondo, Yoshinori
N1 - Funding Information:
This work was financially supported by JSPS KAKENHI Grant Number 19H03346 (Y.K.), 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.), 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.K.). K.H. thanks JSPS for a Fellowship for Young Japanese Scientists (No. 20J20712).
Publisher Copyright:
© 2022 The Royal Society of Chemistry.
PY - 2022/5/9
Y1 - 2022/5/9
N2 - Herein, we report that the organic superbase t-Bu-P4 catalyzes the demethylation reactions of methoxyarenes in the presence of alkanethiol and hexamethyldisilazane. The system can efficiently convert a variety of substrates, including electron-deficient, -neutral, and -rich substrates and heteroaromatic substrates, and displays excellent functional group tolerance. Computational studies show that the high reactivity achieved by t-Bu-P4 is due to the formation of the nucleophilic naked thiolate species.
AB - Herein, we report that the organic superbase t-Bu-P4 catalyzes the demethylation reactions of methoxyarenes in the presence of alkanethiol and hexamethyldisilazane. The system can efficiently convert a variety of substrates, including electron-deficient, -neutral, and -rich substrates and heteroaromatic substrates, and displays excellent functional group tolerance. Computational studies show that the high reactivity achieved by t-Bu-P4 is due to the formation of the nucleophilic naked thiolate species.
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U2 - 10.1039/d2qo00483f
DO - 10.1039/d2qo00483f
M3 - Article
AN - SCOPUS:85135162841
SN - 2052-4110
VL - 9
SP - 3656
EP - 3663
JO - Organic Chemistry Frontiers
JF - Organic Chemistry Frontiers
IS - 14
ER -