A facile and general method for regioselective C2 sulfonylation reaction of indoles mediated by iodine is described. The 2-sulfonylated products were obtained up to 96% yield under mild conditions (room temperature, 2 h).

A highly efficient and generally applicable iodine-catalyzed reaction of arylacetylenic acids arylacetylenes with sodium sulfinates for the synthesis sulfones was developed. The methodology has advantages a metal-free strategy, easy to handle reagents, functional group tolerance, wide range arylacetylenes, access sulfones.

3-(Alkylsulfanyl)- and 3-(arylsulfanyl)indoles were efficiently prepared by the reaction of indoles with sodium sulfinates mediated iodine–PPh3 in ethanol. The salient features present protocol are simplicity, high efficiency, non-anhydrous conditions, environmentally friendly reagents solvent, short time.

A novel method for the asymmetric synthesis of 3,3-difluoro-2-propanoylbicyclo-[3.3.0]octanes involves an unprecedented intramolecular radical cyclization/ipso-1,4-aryl migration cascade.

A novel and expedient method for the decarboxylative sulfonylation of β-aryl-α,β-unsaturated carboxylic acids to their (<italic>E</italic>)-vinyl sulfones is described.

Described herein is a facile electrochemical strategy for the generation of formaldehyde from N,N-dimethylacetamide (DMA) and water (H2O) toward direct site-selective N-hydroxymethylation indoles derivatives. Mechanistic studies suggested that N-(hydroxymethyl)-N-methylacetamide generated in situ DMA/H2O under conditions serves as surrogate. The developed methodology features mild, base- metal catalyst-free conditions. reaction can accommodate broad range substrate scopes offers an...

A practical synthesis of chiral β‐trifluoromethyl‐β‐amino acids is reported by using water as a reaction medium to facilitate the diastereoselective aza‐Michael addition aromatic amines β‐trifluoromethyl‐α,β‐unsaturated oxazolidinone. variety could serve suitable nucleophile that readily undergo nucleophilic conjugate at ambient temperature provide corresponding acid derivatives in excellent combined yields (up 97%) with moderate good diastereoselectivities 3:1). Being complementary...

A consecutive two‐step radical‐mediated cyclization of gem‐difluoromethylenated bis(3‐arylpropagyl)‐indane‐1,3‐diones to access structurally unique cedrenes is described. Substituents located on the aryl rings two propagyl units play an important role in governing pattern. Upon treatment 1,3‐diane with Bu3SnH/AIBN, a tributylstannyl radical between diyne chemoselectively took place, leading corresponding acoradienes good yields, after removal group by TFA. Subsequently, Bu3SnH/AIBN promoted...

The enantioselective protonation of prochiral enolates is an ideal and straightforward platform to synthesize stereodefined α-tertiary esters, which are recurring motifs in a myriad biorelevant molecules important intermediates thereof. However, this approach remains onerous, particularly when dealing with α-unactivated esters related acids, as enantioinduction on the nascent nucleophile necessitates peremptory reaction conditions, thus far only achieved via preformed enolates. A...

The allylic substitution of sterically hindered (2-iodocycloalkyl)phosphates proceeds with complete anti SN2' stereoselectivity mixed diorganozincs the type RZnCH2SiMe3 in presence CuCN·2LiCl. Only group R copper−zinc reagent is transferred substitution. This method was used to prepare odoriferous substances such as (R)-α-ionone 97% ee and (R)-dihydro-α-ionone 98% ee.

Abstract An improved one-pot method to synthesize vinyl sulfones from unsaturated systems by using molecular iodine/sodium arenesulfinate/sodium acetate as reagents was described. Vinyl derived styrene derivatives were generally obtained in good excellent yields except for those bearing strong electron releasing substituent. Aliphatic alkenes and activated gave the corresponding sulfone products moderate yields. Arylacetylenes yielded respective β-iodovinyl while low yield observed with...

Divergent synthesis of <italic>N</italic>-alkyl-3-sulfonylindoles and <italic>N</italic>-alkyl-3-sulfanylindoles from 2-alkynyl-<italic>N</italic>,<italic>N</italic>-dialkylanilines sulfonyl hydrazides has been described.

Malonic acid and derivatives have been well-known to undergo monodecarboxylation under relatively mild conditions exclusively used as a C2 synthon. We report herein their new application C1 synthon via double decarboxylation promoted by sulfur dimethyl sulfoxide. In the presence of amines nucleophiles, wide range thioureas thioamides well N-heterocycles were obtained in good excellent yields heating conditions.

ADVERTISEMENT RETURN TO ISSUEPREVLetterNEXTFour-Component Benzyne Coupling Reactions: A Concise Total Synthesis of Dehydroaltenuene BDarunee Soorukram, Tao Qu, and Anthony G. M. Barrett*View Author Information Department Chemistry, Imperial College London, London SW7 2AZ, England[email protected]Cite this: Org. Lett. 2008, 10, 17, 3833–3835Publication Date (Web):August 2, 2008Publication History Received8 July 2008Published online2 August inissue 1 September...

Treatment of ortho-amino-substituted aryldiyne derivatives with sulfonyl hydrazides in the presence tetrabutylammonium iodide (TBAI) and tert-butyl hydroperoxide (TBHP) led to a cascade cyclization reaction yield sulfonylated indeno[1,2-c]quinolines moderate good yields. The features methodology include metal-free reaction, ease reagent handling, broad functional group tolerance.

Abstract The silver(I)‐mediated decarboxylative fluorination of paraconic acids using Selectfluor ® as a fluorine source is reported. Readily available undergo with mediated by AgNO 3 to give the corresponding β‐fluorinated γ‐butyrolactones in moderate good yields. This approach serves direct and site‐selective strategy for introduction atom at β position γ‐butyrolactone cores. fluorinated products are synthetically useful scaffolds organic synthesis.

An efficient trifluoromethylation of 2-isocyanobiaryls was developed through the constant current electrolysis, employing sodium trifluoromethanesulfinate (CF3SO2Na) as trifluoromethyl source. The method enabled syntheses a series 6-(trifluoromethyl)phenanthridine derivatives in moderate to high yields under metal- and oxidant-free conditions. A gram-scale synthesis highlights synthetic versatility reported protocol.

A formal total synthesis of (+)-estrone (4% overall yield; ca. 12 steps) could be achieved via the Torgov diene. An asymmetric allylic substitution is key step for construction chiral quaternary carbon center a synthetic intermediate which was converted in four steps to

Fluoride-catalyzed stereoselective nucleophilic addition of PhSCF(2)SiMe(3) (1) to α-carboethoxycycloalkanones 2 followed by intramolecular radical cyclization the resulting cis-3 adduct afforded corresponding gem-difluoromethylenated bicyclic compounds 4, which underwent ring-expansion Baeyer-Villiger-type oxidation macrocyclic ketone intermediates give lactones 5.

An efficient C1-difluoromethylation of tetrahydroisoquinolenes was achieved using TMSCF2SPh as a difluoromethylating agent and 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (TEMPO+BF4-) an oxidant. The process provides access to variety C1-difluoro(phenylsulfanyl)methylated tetrahydroisoquinoline adducts in good yields. These were employed key precursors for preparing fluorinated pyrrolo[2,1-a]isoquinoline benzo[a]quinolizidines.

A novel and efficient sequential cross-coupling/annulation strategy is developed to construct structurally optoelectronically diverse class of dibezopleiadiene-embeded polyaromatics.

Persulfate-promoted radical cascade trifluoromethylthiolation and cyclization of 3-alkyl-1-(2-(alkynyl)phenyl)indoles with AgSCF3 were investigated. This protocol provides a novel route to CF3S-substituted indolo[1,2-a]quinoline-7-carbaldehydes indolo[1,2-a]quinoline-7-methanone derivatives via the formation C-SCF3 bond C-C benzylic carbon oxidation in single step. reaction can accommodate broad range functional groups. The single-crystal X-ray diffraction data confirm chemical structure...

Abstract Thiourea derivatives are in‐demand motifs in organic synthesis, medicinal chemistry and material science, yet redox methods for the synthesis that start from safe, simple, inexpensive readily available feedstocks scarce. In this article, we disclose of these using elemental sulfur nitromethane as starting materials. The method harnesses multi‐electron auto‐redox property presence amines, delivering thiourea products without any added oxidant or reductant. Extension reaction to...