Iridium-Catalyzed Oxidative Olefination of Furans with Unactivated Alkenes

Abstract

The oxidative coupling of arenes and alkenes is an attractive strategy for the synthesis of vinylarenes, but reactions with unactivated alkenes have typically occurred in low yield. We report an Ir-catalyzed oxidative coupling of furans with unactivated olefins to generate branched vinylfuran products in high yields and with high selectivities with a second alkene as the hydrogen acceptor. Detailed mechanistic experiments revealed catalyst decomposition pathways that were alleviated by the judicious selection of reaction conditions and application of new ligands.

[Cu(NHC)]‐Catalyzed C−H Allylation and Alkenylation of both Electron‐Deficient and Electron‐Rich (Hetero)arenes with Allyl Halides

“…[15] Forthis purpose,p alladium catalyst systems were previously developed, including the Fujiwara-Moritani reaction. [17] In this context, the development of efficient and selective catalytic systems based on the first-row transition metals is highly desirable. [17] In this context, the development of efficient and selective catalytic systems based on the first-row transition metals is highly desirable.…”

Rhodium‐Catalyzed Intramolecular C−H Silylation by Silacyclobutanes

“…Similar to our previous observations, [10b] ligands with different dihedral angles showed dramatically different reactivity.T he less hindered ligand spirophos and BINAP were ineffective (entries 2-3). Among these ligands,T MS-segphos [20] gave the best result (52 %y ield, entry 7). As ystematic screening of ligands with segphos backbone that possess wider dihedral angles [19] was then conducted (entries 5-8).…”

Rhodium‐Catalyzed Intramolecular C−H Silylation by Silacyclobutanes

“…As ystematic screening of ligands with segphos backbone that possess wider dihedral angles [19] was then conducted (entries [5][6][7][8]. Among these ligands,T MS-segphos [20] gave the best result (52 %y ield, entry 7). Further increasing the bulkiness,e ither by using larger 3, 5-ditriethylsilylphenyl (TES) [21] or by employing C1-tunephos [22] Figure 1.…”