Oxidative Coupling between Two Hydrocarbons: An Update of Recent C–H Functionalizations

Gold-Catalyzed Oxidative Coupling of Alkynes toward the Synthesis of Cyclic Conjugated Diynes

“…37 In that study, we discovered that oxidative coupling of terminal alkynes could be achieved using a gold catalyst under suitable conditions (Phen as ligand and bisacetoxyiodobenzene(PIDA) as oxidant). When comparing with the copper-promoted Glaser-Hay conditions, 38–41 gold catalysts gave excellent cross-coupling selectivity between aromatic alkynes and aliphatic alkynes. Besides the excellent selectivity, we also observed a much faster reaction rate with gold-catalyzed condition over the copper.…”

Redox-Induced Aromatic C–H Bond Functionalization in Metal Complex Catalysis from the Electrochemical Point of View

“…Transition-metal-catalyzed direct C-H functionalizations open a new road for diverse C-C, C-P, and C-N bond construction in a one-step and atom economical way, without the requirement of prefunctionalized C-H coupling partners [1][2][3][4][5][6]. The cleavage of high energy C-H bonds (E~110 kcal·mol −1 for C(aryl)-H bonds) typically requires harsh reaction conditions that result in limited substrate scope and low functional group tolerance.…”

“…The chemistry of palladium (Pd) compounds in higher oxidation states is extremely useful in oxidative functionalizations, in which a C-H bond can be catalytically converted into another functional group [1,[6][7][8][9][10][11][12]. One of the major problems in Pd(II)/Pd(III)/Pd(IV) chemistry, however, is that the co-oxidants used are either expensive to purchase (silver and other metal salts are often used), or to separate from the product mixture (particularly in the case of high molecular weight organic oxidants).…”

Oxidative Coupling in Complexity Building Transforms

“…The oxidative coupling of similar enolizable substrates with stoichiometric bases and oxidants enjoys a long history 8 with more recent efforts to effect cross couplings as illustrated in Scheme 2d. 5 Such constructions allow access to more complex skeletons poised for additional bond constructions leading toward biologically interesting structures as seen in the case of hapalindole U.…”