Remote C(sp3)—H insertion into non-activated bonds: rapid construction of an added-value molecular diverse library



The synthesis of added-value compounds from raw feedstock materials represents one of the major challenges in synthetic organic chemistry. By using a well-defined intramolecular C—H insertion reaction, it is possible to transform a number of raw feedstock compounds into a library of molecularly complex and diverse compounds. In addition, these compounds display a C—Br bond amenable for further functionalization. A preliminary mechanistic study supports the participation of an elusive gold (I) vinylidene complex as key intermediate of the reaction. The most salient feature of this methodology is the ability to functionalize in a predictable way non-activated C—H bonds without any sort of electronic, geometric or conformational bias.

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Revised version of both the main text and the supporting information


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Supplementary material

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Experimental procedures and spectroscopic data
Experimental procedures for the synthesis of starting materials and final products. Full caracterization of staring materials and final products. KIE determination experiments. 13C isotope labelling experiments. X-ray structures