Synthesis of [N,P] ligands based on pyrrole. Application to the total synthesis of arnottin I

• Published in: Tetrahedron Vol. 70; no. 7; pp. 1422 - 1430
• Main Authors: Suárez-Meneses, Jesús V., Bonilla-Reyes, Edgar, Blé-González, Ever A., Ortega-Alfaro, M. Carmen, Toscano, Rubén Alfredo, Cordero-Vargas, Alejandro, López-Cortés, José G.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 18.02.2014; Elsevier
• Subjects: [N,P] ligands; Arnottin I; Chemistry; Chemistry, Organic; Couplings; Donors (electronic); Electronics; Esters; Ligands; Pd coupling; Phosphines; Physical Sciences; Pyrroles; Science & Technology; Synthesis (chemistry); Total synthesis; Pd coupling; [N,P] ligands; Arnottin I; Total synthesis; NICKEL-COMPLEXES; CHELERYTHRINE; 1ST EVIDENCE; NATURAL-PRODUCTS; OXAZOLINE-CONTAINING LIGANDS; SUZUKI REACTION; P,N LIGANDS; CROSS-COUPLING REACTIONS; PALLADIUM-CATALYZED CARBONYLATION; ARYL
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2014.01.002

This paper describes the synthesis of a new class of [N,P] ligands based on pyrrole with a dimethylamino group as hard donor and a phosphine moiety as soft base. We have also modified the phosphine fragment to change the electronic and steric properties of these ligands. Palladium complex 3a proved to be very efficient in Heck cross-coupling reactions and in intramolecular aryl–aryl couplings of esters and amides. We have demonstrated the applicability and efficiency of this novel catalyst in the total synthesis of the natural product arnottin I. [Display omitted]