Palladium-Catalyzed Oxidative Cross-Coupling of 2-Phenylphenols with Alkenes

Abstract

2-Phenylphenols react with alkenes such as acrylate esters in the presence of a palladium-copper catalyst system under air to give the corresponding 6-substituted 6H-dibenzo[b,d]pyran derivatives.

Oxidative Coupling of Aromatic Substrates with Alkynes and Alkenes under Rhodium Catalysis

“…After a 15 year hiatus, early examples of the catalytic version involving a Pd II /Pd 0 cycle were reported (Scheme ) 4. Thus, we succeeded in conducting the palladium‐catalyzed oxidative coupling of 2‐phenylphenols,4a N ‐sulfonyl‐2‐phenylanilines,4b and benzoic acids4b with alkenes by using Cu(OAc) 2 and air as the cocatalyst and terminal oxidant, respectively. The catalytic ortho ‐vinylation of acetoanilides was also reported by de Vries and co‐workers 4c.…”

Pd(II)-Catalyzed ortho- or meta-C–H Olefination of Phenol Derivatives

“…Early studies by Rawal and Miura used the phenol to direct arylation of biphenyls with ArI and Pd(0)/PPh 3 catalysts. 4 Bedford and others succeeded in using catalytic amount of phosphites as directing groups to promote Rh(I)-catalyzed ortho -arylation of phenols (Fig 1). 5 Hartwig reported Ir(I)-catalyzed borylation of hydrosilyl ethers of phenols.…”

Catalytic 1,4‐Rhodium(III) Migration Enables 1,3‐Enynes to Function as One‐Carbon Oxidative Annulation Partners in CH Functionalizations

“…This regioselectivity is maintained in the oxidative annulation of 1,3-enynes, as demonstrated by the groups of Fagnou (Scheme 1 a) [6a] and Ackermann,[6b] for example. Herein, we describe a new mode of oxidative annulation, in which 1,3enynes are able to function as one-carbon, [7] rather than twocarbon reaction partners (Scheme 1 b). We propose this reactivity arises from a hitherto rare example of 1,4-Rh III migration, which opens up new possibilities in CÀH functionalization reactions.…”