Carboxylic acid reductions: Insights from mixed anhydrides and thiol esters

Metal-Catalyzed Carbon−Sulfur Bond Formation

“…The search for new methods for the preparation of thiol esters and sulfur-containing γ-lactones is a topic of current interest . Not only do these compounds constitute a group of natural products, but they are also attractive building blocks in the synthesis of complex organic molecules. , Palladium(0) complexes were found to exhibit excellent catalytic activity toward the thiocarbonylation of propargylic alcohols, affording thiofuranones, thioesters, or dithioesters as the principal product, depending on the reaction conditions (eq 57), which represents one of the most straightforward routes to these compounds.

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The First Examples of the Palladium-Catalyzed Thiocarbonylation of Propargylic Alcohols with Thiols and Carbon Monoxide

“…The search for new methods for the preparation of thiol esters and sulfur-containing γ-lactones is a topic of current interest. , Not only do these compounds constitute a group of natural products, but they are also attractive building blocks in the synthesis of complex organic molecules . The reaction described herein (eq 1) represents one of the most straightforward routes to these compounds.…”

Aldehydes and ketones

“…Using this procedure, Seyferth et al have prepared and trapped this species with various ele~trophiles.~~ An alternative, and practically simpler, procedure is to lithiate the equivalent thioester at -78°C. 32 Quenching the resulting anion with an electrophile then affords the corresponding ketone or aldehyde. The latter may also be obtained from the starting thioester by treatment with Bu,SnH and a Pdo catalyst.…”