Gold(I)‐Catalyzed Intramolecular C(sp 3 )−H Insertion by Decarbenation of Cycloheptatrienes | Zendy

Yin Xiang | Zendy; Zuccarello Giuseppe | Zendy; GarcíaMorales Cristina | Zendy; Echavarren Antonio M. | Zendy

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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.

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