Gold(I)-Catalyzed Intramolecular C(sp3)−H Insertion by Decarbenation of Cycloheptatrienes |
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| Authors: | Xiang Yin Giuseppe Zuccarello Cristina García-Morales Prof Dr Antonio M Echavarren |
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| Institution: | Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology (BIST), Av. Països Catalans 16, 43007 Tarragona, Spain |
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| Abstract: | A novel synthesis of indanes and dihydronaphtalenes based on the intramolecular insertion into C(sp3)−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(sp3)−H functionalization process. |
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| Keywords: | carbenes C−H insertion decarbenation gold catalysis indanes |
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