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Dearomatizing and Derivatizing a Mesityl Group on Boron by One‐Pot Photoisomerization and [4+2] Diels–Alder Addition
Author(s) -
Deng Billy,
Wang Xiang,
Wang Suning
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201903534
Subject(s) - photoisomerization , chemistry , ring (chemistry) , chelation , conjugated system , boron , aryl , diels–alder reaction , transformation (genetics) , medicinal chemistry , photochemistry , organic chemistry , isomerization , catalysis , alkyl , polymer , biochemistry , gene
Boron compounds having a conjugated chelate backbone (N,C‐chelate or C,C‐chelate) and two mesityl substituents on boron have been found to undergo a facile one‐pot transformation/reaction with dienophiles, which leads to the dearomatization of one mesityl ring and its [4+2] Diels–Alder addition with the dienophile. Photochemical activation is the key in this transformation of the aryl ring.