Rhodium-Catalyzed [2 + 2 + 2] Cyclotrimerizations of Yndiamides with Alkynes

Yndiamides offer opportunities for the synthesis of vicinally nitrogen-disubstituted aromatics and azacycles. Here we report the Rh-catalyzed cyclotrimerization of alkynyl yndiamides with alkynes, the regiochemical outcome of which is controlled by the electronic properties of the alkyne partner, en...

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Veröffentlicht in:Organic letters 2022-10, Vol.24 (41), p.7522-7526
Hauptverfasser: Smith, Philip J., Tong, Zixuan, Ragus, Julia, Solon, Pearse, Shimkin, Kirk W., Anderson, Edward A.
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Sprache:eng
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Zusammenfassung:Yndiamides offer opportunities for the synthesis of vicinally nitrogen-disubstituted aromatics and azacycles. Here we report the Rh-catalyzed cyclotrimerization of alkynyl yndiamides with alkynes, the regiochemical outcome of which is controlled by the electronic properties of the alkyne partner, enabling the formation of 7-aminoindolines with excellent selectivity (up to >20:1 r.r.). We also report a complementary synthesis of bicyclic 1,2-dianiline derivatives by cyclotrimerization of yndiamides with terminal diynes, where slow addition of the diyne overcomes self-dimerization.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02770