Intermolecular Palladium‐Catalyzed Oxidative Fluorocarbonylation of Unactivated Alkenes: Efficient Access to β‐Fluorocarboxylic Esters

Abstract

A novel palladium-catalyzed intermolecular oxidative fluorocarbonylation of alkenes has been developed, in which employment of a cooperative process with electrophilic ArIF -meidated alkenes activation and palladium-catalyzed carbonylation is crucial for the successful catalytic transformation. The current transformation presents the first convenient method to generate β-fluorinated carboxylic acid derivatives under mild reaction conditions from simple alkenes with excellent regioselectivity.

Copper-Catalyzed Carbonylative Synthesis of β-Boryl Amides via Boroamidation of Alkenes

“…In summary, a new strategy on copper-catalyzed regioselective carbonylative boroamidation of olefins has been developed. [57][58][59] By the using hydroxylamines as the electrophilic amines, various alkenes were reacted successfully and gave the desired ß-boryl amides in good to excellent yields. Ethylene gas can be successfully transformed as well.…”

Acetyl Coenzyme A Analogues as Rationally Designed Inhibitors of Citrate Synthase

“…The corresponding defluoro‐hydro analogue 12 was prepared as illustrated in Scheme . Amine 36 was released after hydrazine treatment of pent‐4‐enyl‐ N ‐phthalimide 35 , which was itself prepared as previously described . Coupling of 36 with pantothenic acid 21 generated amide 37 , and then basic hydrolysis provided access to diol 38 for biotransformation.…”

Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes

“…Compared to the diverse reactivity profiles of transition metal-catalyzed functionalization of alkenes, hypervalent iodine (III)-mediated reactions are limited to nucleophilic substitution processes. Recently, Liu and co-workers reported a novel cooperative strategy by combining palladium catalysis and hypervalent iodine-mediated reactions to achieve the intermolecular oxycarbonylation [ 79 ], azidocarbonylation [ 80 ] and fluorocarbonylation [ 81 ] of alkenes. Mechanistic studies showed that PhI(OAc) 2 is activated by the aid of BF 3 ·OEt 2 and then reacts with an alkene to form a three-membered iodonium ion intermediate 75 .…”