TY - JOUR
T1 - Catalytic amide base system generatedin situfor 1,3-diene formation from allylbenzenes and carbonyls
AU - Shigeno, Masanori
AU - Kajima, Akihisa
AU - Nakaji, Kunihito
AU - Nozawa-Kumada, Kanako
AU - Kondo, Yoshinori
N1 - Funding Information:
This work was financially supported by JSPS KAKENHI Grant Number 19H03346 (YK), JSPS KAKENHI Grant Number 19K06967 (MS), the Environment Research and Technology Development Fund (JPMEERF20202R02) of the Environmental Restoration and Conservation Agency of Japan (MS), The Uehara Memorial Foundation (MS), Grand for Basic Science Research Projects from The Sumitomo Foundation (MS), Yamaguchi Educational and Scholarship Foundation (MS), NIPPON SHOKUBAI Award in Synthetic Organic Chemistry, Japan (MS), and also the Platform Project for Supporting Drug Discovery and Life Science Research funded by Japan Agency for Medical Research and Development (AMED) (MS, KNK, and YK).
Publisher Copyright:
© The Royal Society of Chemistry 2020.
PY - 2021/2/7
Y1 - 2021/2/7
N2 - The amide base generatedin situfrom tetramethylammonium fluoride and N(TMS)3catalyzes the synthesis of 1,3-diene from an allylbenzene and carbonyl compound. The system is applicable to the transformations of a variety of allylbenzenes with functional groups (halogen, methyl, phenyl, methoxy, dimethylamino, ester, and amide moieties). Acyclic and cyclic diaryl ketones, pivalophenone, pivalaldehyde, and isobutyrophenone are used as coupling partners. The role oftransβ-methyl stilbenes in product formation is also elucidated.
AB - The amide base generatedin situfrom tetramethylammonium fluoride and N(TMS)3catalyzes the synthesis of 1,3-diene from an allylbenzene and carbonyl compound. The system is applicable to the transformations of a variety of allylbenzenes with functional groups (halogen, methyl, phenyl, methoxy, dimethylamino, ester, and amide moieties). Acyclic and cyclic diaryl ketones, pivalophenone, pivalaldehyde, and isobutyrophenone are used as coupling partners. The role oftransβ-methyl stilbenes in product formation is also elucidated.
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U2 - 10.1039/d0ob02007a
DO - 10.1039/d0ob02007a
M3 - Article
C2 - 33146220
AN - SCOPUS:85100797097
SN - 1477-0520
VL - 19
SP - 983
EP - 987
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 5
ER -