Aldehyde arylation

All lation of Garbanions. Concentrated N a OH—hen syl triethyl amm onium chloride is the base/catalyst system normally used for this type of process (20). Classes of compounds alkylated in this way include phenylacetonitriles, ben2ylketones, simple aUphatic ketones, certain aldehydes, aryl sulfones, P-ketosulfones, P-ketoesters, malonic esters and nitriles, phenylacetic esters, indene, and fluorene (see Alkylation). 

In a synthesis of decinine a phenol was protected as a methanesulfonate that was stable during an Ullman coupling reaction and during condensation, catalyzed by calcium hydroxide, of an amine with an aldehyde. Aryl methanesulfonates are cleaved by warm sodium hydroxide solution. " ... 

Since Wakamatsu serendipitously discovered amidocarbonylation while performing the cobalt-catalyzed hydroformyla-tion of olefins in 1971, this unique carbonylation reaction, affording a-amino acids directly from aldehydes, has been extensively studied.More recently, palladium-catalyzed processes have been developed to expand the scope of this reaction.The Pd-catalyzed amidocarbonylation has been applied to aldehydes,aryl halides, and imines. As a related reaction, lactamization " of aryl halides catalyzed by a rhodium complex has also been developed. 

Reaction of the Titanated Bislactim Ether. The titanium derivative of the bislactim ether of cyclo(L-Val-Gly) reacts with alkyl aldehydes, aryl aldehydes, and a,(3-unsaturated aldehydes highly diastereoselectively to give almost exclusively the syn addition products (eq 2). Hydrolysis with dilute Trifluo-roacetic Acid affords (2R, 35 )-(3-hydroxy-a-amino acid methyl esters. a-Amino-y-nitro amino acids can be obtained by 1,4-addition of the titanated bislactim ether to nitroalkenes and subsequent hydrolysis of the adduct. ... 

Hollingworth, G. J. Aldehydes Aryl and heteroaryl aldehydes, in Comp. Org. Funct. Group Trans, (eds. Katritzky, A. R., Meth-Cohn, 0.,Rees, C. W.), 3, 81-109, 733-856 (Pergamon, Oxford, New York, 1995). 

Arylation of aldehydes. Aryl group transfer from arylboronic acids to relatively... 

Corynantheine aldehyde-aryl- H (157) G. ledgeriana Quinine Cinchonidine Cinchonine None 40... 

Reductions. The InCIj-Bu SnH/PhjP combination (catalytic in indium) reduces acid chlorides to aldehydes." Aryl ketones and secondary benzyl alcohols are deoxygenated with hydrosilanes using InCl, as cataly.st." Deoxygenative allylation of aryl ketones occurs when allyltrimethylsilane is added. ... 

Aldehydes. Aryl, heterocyclic, and vinylic halides react at 80-150° under about 1000 psi of carbon monoxide and hydrogen (1 1) in the presence of these palladium complexes as catalysts and a tertiary amine (1 eq.) to give aldehydes, usually in good yields. The reaction is actually believed to involve a series of... 

Oxone has also been recently more thoroughly studied as reagent for the oxidation of aldehydes. Aryl- and aliphatic aldehydes can be efficiently converted directly to acids or esters depending on the choice of solvent (eq 34). They can also be converted to nitriles in one pot by reaction with hydroxylamine on alumina with microwave irradiation (eq 35). ... 

In the presence of tetrafluoroboric acid, aliphatic aldehydes, aryl ketones and orthoesters react similarly [129]. 

To date, no report has appeared using manganese metal. We wish to report a mild method for reductive coupling reactions of aryl aldehydes, aryl ketones, andaldimines [100]. 

CO Vibrations Saturated aliphatic aldehydes ajS-unsaturated aldehydes ajS-y(5-unsaturated aldehydes Aryl aldehydes... 

O -Amino Phosphonate Aminosulfonylcarbamate -Amino Thioester Ammonium Salt Anhydride Aryl Aldehyde Aryl Alkyne Aryl Amine... 

---