Recent Advances in Cross‐Dehydrogenative Couplings (CDC) of C−H Bond in Aqueous Media

Abstract

To develop highly efficient synthetic reactions is quite important in organic chemistry. Cross dehydrogenative couplings (CDC) utilize C−H bonds of substrates to construct new C−X (X=C, S, O, N, P) bonds. For CDC, the pre‐functionalization of reaction substrates can be avoided and the C−X (X=C, S, O, N, P) bonds can be newly formed by simple and efficient synthesis routes. Meanwhile, water is increasingly used as a substitute for organic solvents in cross‐dehydrogenative coupling because of its rich content, non‐toxicity, and non‐ flammability. In recent years, organic chemists are devoted their efforts to explore the cross dehydrogenative couplings (CDC) in aqueous phase which feature high atom utilization rate and environmental friendliness. Herein, we summarized the recent advances in the construction of C−C, C−S, C−O, C−N, and C−P bonds through CDC reactions of C−H bonds in water.

Carbon‐Sulfur Bond Constructions: From Transition‐Metal Catalysis to Sustainable Catalysis

“…Various CÀ C, CÀ S, CÀ N, CÀ O, CÀ Se bond forming reactions have been carried out under oxidant catalysis. [26] These reactions proceed via a radical mechanism. In presence of oxidant the formation of carbon radical takes place.…”

Progress of Dialkyl Azodicarboxylates in Organic Transformations

“…[12][13][14] However, in recent past, the oxidative abilities of these azo compounds have been investigated in other organic transformations. Oxidative coupling or cross dehydrogenative coupling (CDC) [15][16][17] and oxidative Ugi-type reaction sequence [18] require oxidant, and dialkyl azodicarboxylates are suitable candidates for these oxidation reactions. Transition metal catalyzed CÀ H activation reactions have been investigated over the past two decades and proved to be an effective methodology for CÀ H functionalization in various substrates.…”

Iron-catalyzed domino coupling reactions of π-systems

“…Besides the more recognized concept of TM cross-coupling reactions revolving around an organic electrophile bearing a leaving group and an organometallic nucleophile, there is another large area of cross-coupling reactions that have been under significant development over the past 10 years. First achieved by Li and co-workers in 2007 [ 44 ], cross-dehydrogenative-coupling (CDC) reactions offer a highly atom economic approach to carbon–carbon (C–C) and carbon–heteroatom (C–X) bond formation via C–H activation [ 45 – 46 ]. Generally speaking, C–C bond forming reactions can be classified into three types ( Scheme 1 ): the reaction of a compound bearing functional group (X), coupling with another compound bearing functional group (Y), producing a new C–C bond through the formation of X–Y ( Scheme 1a ).…”