Synthesis of 1,4‐Cyclohexadiene Carboxylates through a Formal [2+4]‐Cycloaddition of Propiolates under Cobalt Catalysis

• Published in: Helvetica chimica acta Vol. 103; no. 12
• Main Authors: Charpentier, Julie, Voirol, Francis, Flachsmann, Felix, Tanner, Silvia, Aeberli, Natalie, Brunner, Gerhard, Goeke, Andreas
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 01.12.2020; Wiley Subscription Services, Inc
• Subjects: alkynes; Aromatic compounds; Carboxylates; Catalysis; Catalysts; Chemistry; Chemistry, Multidisciplinary; Cobalt; Cycloaddition; cyclohexadiene; Dienes; Flowers; fragrance chemistry; Odor; Odors; Physical Sciences; Science & Technology; cyclohexadiene; fragrance chemistry; cycloaddition; DIELS-ALDER REACTIONS; 1,3-DIENES; COBALT(I)-CATALYZED 6+2 CYCLOADDITIONS; alkynes; COMPLEXES; catalysis; cobalt; BIRCH REDUCTION

A low‐valent cobalt(I) complex, formed from the reduction of CoBr2(dppe) with zinc, acts as catalyst for the efficient [2+4] cycloaddition of β‐alkyl, cycloalkyl and aryl substituted propiolates to dienes. This transformation yields synthetically relevant 1,4‐cyclohexadiene carboxylates in good to e...