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Gold(I)‐Catalyzed Intramolecular C(sp 3 )−H Insertion by Decarbenation of Cycloheptatrienes
Author(s) -
Yin Xiang,
Zuccarello Giuseppe,
GarcíaMorales Cristina,
Echavarren Antonio M.
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.201900919
Subject(s) - intramolecular force , carbenoid , carbene , chemistry , catalysis , deuterium , osmium , kinetic isotope effect , reductive elimination , photochemistry , insertion reaction , stereochemistry , medicinal chemistry , rhodium , organic chemistry , physics , quantum mechanics , ruthenium
A novel synthesis of indanes and dihydronaphtalenes based on the intramolecular insertion into C(sp 3 )−H bonds of gold(I) carbenes generated by retro‐Buchner reaction (decarbenation) has been developed. Deuterium‐labeling and kinetic isotope effect experiments, DFT calculations, and generation of the proposed carbene intermediate from a well‐characterized gold(I) carbenoid support the involvement of a three‐center concerted mechanism for the C(sp 3 )−H functionalization process.