Carboalkoxylation of aryl and benzyl halides catalyzed by dichlorobis(triphenylphosphine)palladium(II)

Abstract

65 7.0 C6HgCH2N(CH3)2 (100, 85s) 25 2.0 (< 5) ch3(ch2)5n(ch3)3i 15066-77-0 65 4.0 CH3(CH2)5N(CH3)2 (100, 884) 25 2.0 (< 5) ch3c(ch3)2ch2c(ch3)2n(ch3)3i 53624-41-8 65 1.0 ch3c(ch3)2ch2c(ch3)2n(ch3)2 (100) " Reductions were performed using 1.0 mmol of salt and 1.5 mmol of LiEt3BH in 5 ml of dry THF under nitrogen.6 All products identified by comparison with authentic samples or through preparation of known derivatives of isolated products. c Yields were determined by glpc analysis with the aid of an internal standard unless otherwise noted.d Yield of isolated picrate salt.

Trans-chelating ligands in palladium-catalyzed carbonylative coupling and methoxycarbonylation of aryl halides

“…The formation of the by-produced 2-bromobenzoic acid in the entries 3e and 3j (Table 1) urged to test the applicability of the catalyst 2 to other carbonylation reactions, for example, methoxycarbonylation of aryl halides. Although the progress recently achieved in the field of alkoxycarbonylation of aryl halides is spectacular [9,34] and relatively simple catalysts efficiently promote the transformation of aryl iodides [35], bromides [36] and even chlorides [30,37] into carboxylic acid derivatives under relatively mild conditions, the quest after new catalytic systems is not over.…”

An 8‐Fold Parallel Reactor System for Combinatorial Catalysis Research

“…The reaction selected for determining precision and screening reaction parameters was carbonylation of iodobenzene to methylbenzoate using a palladium catalyst (see Figure 11) as described in the literature [14]. …”

An Enantiospecific Synthesis of Jiadifenolide

“…After a reductive cleavage of the oxime acetate group in 11 by the method of Weinreb, [21] the resulting C-6 ketone was advanced to vinyl triflate 12 by a reaction of the derived enolate ion with Comins’s reagent. [22] A palladium-catalyzed carbomethoxylation [23] of 12 afforded 13 and was followed by a base-induced methanolysis of the acetate ester with concomitant lactone ring formation. Interestingly, this method for lactonizing 13 afforded a mixture of compounds 14 , 15 , and 16 (Scheme 2); however, this three-component mixture was transformed to a single epoxy bislactone, compound 17 , on treatment with hydrogen peroxide and sodium hydroxide.…”