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

ABSTRACT: 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.

SUBMITTER: Smith PJ

PROVIDER: S-EPMC9594354 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

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

Smith Philip J PJ Tong Zixuan Z Ragus Julia J Solon Pearse P Shimkin Kirk W KW Anderson Edward A EA

Organic letters 20221010 41

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 yndiamid ...[more]

PMID: 36214595

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