Gold(i)-catalysed high-yielding synthesis of indenes by direct Csp3–H bond activation. Issue 40 (27th September 2018)

• Record Type: Journal Article
• Authors: Nahide, Pradip D.; Jiménez-Halla, J. Oscar C.; Wrobel, Katarzyna; Solorio-Alvarado, César R.; Ortiz Alvarado, Rafael; Yahuaca-Juárez, Berenice
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 40(2018)
• Page Start: 7330
• Page End: 7335
• Publication Date: 2018-09-27
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob02056f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A catalytic, practical and high-yielding procedure for the synthesis of indenes by direct Csp 3 –H activation under gold(i ) catalysis was developed. Abstract : A catalytic, practical and high-yielding procedure for the synthesis of indenes by direct Csp 3 –H activation under gold(i ) catalysis was developed. The scope of the protocol was determined by synthesizing some electron-neutral, electron-poor as well as electron-rich derivatives including the dibenzofurane and carbazole heterocycles. The mechanism of this reaction was elucidated by theoretical calculations using a ONIOM(M08-HX/mixed-basis:PM6) hybrid scheme. Thereby we found a pericyclic transformation involving a [1, 5]-H shift generating a gold(i )–carbene that evolves to the indene derivative. In comparison with several reports, our protocol presents a direct activation of the Csp 3 –H bond.