New Odorless Protocols for the Synthesis of Aldehydes and Ketones from Thiol Esters

  title={New Odorless Protocols for the Synthesis of Aldehydes and Ketones from Thiol Esters},
  author={Tohru Miyazaki and Yuki Han-ya and Hidetoshi Tokuyama and Tohru Fukuyama},
Dodecanethiol esters derived from odorless dodecanethiol proved to be suitable substrates for Pd-catalyzed reduction with triethylsilane, coupling with organozinc reagents, and coupling with terminal acetylenes. 
19 Citations
Synthesis of diaryl ketones via a phosphine-free Fukuyama reaction.
The synthesis of unsymmetrical diaryl ketones via the Fukuyama coupling of thioesters and organozinc reagents is described and the simple complex, Pd(dba)(2), was found to convert a variety of aryl thioester to diarylketones in good yields.
The palladium-catalyzed cross-coupling of N-heteroaryl sulfides with organozinc reagents was developed. Scope and limitation of the reaction regarding generality of zinc reagents and substrate were
Nickel-Catalyzed Thiocarbonylation of Arylboronic Acids with Sulfonyl Chlorides for the Synthesis of Thioesters.
An interesting procedure for thioester synthesis via nickel-catalyzed thiocarbonylation of arylboronic acid with sulfonyl chlorides as the sulfur source has been explored and a broad range of thioesters were obtained.
Autocatalytic Synthesis of Thioesters via Thiocarbonylation of gem-Difluoroalkenes.
A new method for the synthesis of acyethanethioates via thiocarbonylation of gem-difluoroalkenes with thiols with in situ generated HF facilitated the C-F bond cleavage in an autocatalytic manner.
L-Proline Derived Bifunctional Organocatalysts: Enantioselective Michael Addition of Dithiomalonates to trans-β-Nitroolefins.
A series of novel L-proline derived tertiary amine bifunctional organocatalysts 9 are reported, which were applied to the asymmetric Michael addition of dithiomalonates 2 to trans-β-nitroolefins 1, and the synthetic utility was demonstrated in the short synthesis of (R)-phenibut in high yield.
Regioselective Thiocarbonylation of Vinyl Arenes.
A palladium-catalyzed thiocarbonylation of styrene derivatives is reported for the first time, and challenging ortho-substituted styrenes are converted with unprecedentedly high regioselectivity.
Air-Tolerant Direct Thiol Esterification with Carboxylic Acids Using Hydrosilane via Simple Inorganic Base Catalysis.
Various functional groups on carboxylic acid and thiol substituents can be tolerated by the present system to afford thioesters in yields of 19-100%.
Oxalic Acid Monothioester for Palladium-Catalyzed Decarboxylative Thiocarbonylation and Hydrothiocarbonylation.
Oxalic acid monothioester (OAM), an easily accessible and storable reagent, was reported herein as a thioester synthetic equivalent for palladium-catalyzed decarboxylative thiocarbonylation of organohalides and hydrotho-carbon bonds at room temperature with high chemo- and regioselectivity.
Palladium-Catalyzed Reductive Conversion of Acyl Fluorides via Ligand-Controlled Decarbonylation.
Ligand-controlled non-decarbonylative and decarbony lative conversions of acyl fluorides were developed using a Pd(OAc)2/Et3SiH combination and aldehydes were obtained as simple reductive conversion products.
Asymmetric Cycloetherification of in Situ Generated Cyanohydrins through the Concomitant Construction of Three Chiral Carbon Centers.
This protocol facilitates the concise synthesis of optically active tetrahydropyran derivatives, which are ubiquitous scaffolds found in various bioactive compounds, through the simultaneous construction of multiple bonds and stereogenic centers, including tetrasubstituted chiral carbons.