Palladium-catalyzed Tandem Reaction Research Articles

Progress in Palladium-Catalyzed Tandem Reaction of Constructing Benzo-Five-Membered Heterocycles

Progress in Palladium-Catalyzed Tandem Reaction of Constructing Benzo-Five-Membered Heterocycles

A palladium-catalyzed tandem reaction of 2-alkynylbenzenesulfonamides with 2-(2-bromoarylidene)cyclobutanones

The core of benzo[f][1,2]thiazonin-5(4H)-one 3,3-dioxide is efficiently assembled through a palladium-catalyzed tandem reaction of 2-alkynylbenzenesulfonamides with 2-(2-bromobenzylidene)cyclobutanones via double carbometallation. A range of polycycles with a nine-membered sultam ring are generated in moderate to good yields.

Palladium-Catalyzed Triple Cyclization of 2,7-Alkadiynylic Carbonates with Allenes Bearing a Carbon Nucleophile.

Palladium-catalyzed tandem reactions of 2,7-alkadiynylic carbonates with allenes bearing a carbon nucleophile such as malonate and bis(phenylsulfonyl)methane for the efficient syntheses of fused tricycles, such as 3,5,6,7-tetrahydro-1H-indeno[5,6-c]furan, 1,2,3,5,6,7-hexahydrocyclopenta[f]isoindole, and 1,2,3,5,6,7-hexahydro-s-indacene derivatives, have been reported. The reaction forms two five-membered rings and one benzene ring fusing them in the middle.

Tandem Chloropalladation/Cyclization and Dearomative Cyclization toward Functionalized Tricyclic Bridged [3.2.1] Skeleton Compounds.

A palladium-catalyzed tandem reaction is reported that involves chloropalladation/cyclization and dearomative cyclization to construct a tricyclic bridged [3.2.1] carbocyclic-skeleton and oxa- and aza-skeletons. In this domino process, a level of ring strain and other competitive reactions, i.e., protonolysis, β-hydride elimination, and chlorination of the C-Pd bond, were suppressed to the lowest level under mild reaction conditions.

A palladium-catalyzed tandem reaction of 2-(2-bromobenzylidene)cyclobutanone with 2-alkynylphenol.

An efficient approach for the generation of benzo[b]naphtho[2,3-d]oxocin-6-ones through a palladium-catalyzed tandem reaction of 2-alkynylphenol with 2-(2-bromobenzylidene)cyclobutanone is described. This tandem process afforded the fused polycycles easily, with the formation of three bonds with high efficiency, starting from easily available materials. Good functional group tolerance as well as excellent selectivity was displayed.

ChemInform Abstract: Synthesis of 3‐Trifluoromethylbenzofurans via Palladium‐Catalyzed Tandem Elimination/Annulation of β‐Chloro‐β‐(trifluoromethyl)styrenes with 2‐Halophenols.

A palladium-catalyzed tandem elimination and annulation reaction has been developed. In this way, a variety of 3-trifluoromethybenzofurans were prepared in moderate to good yields via tandem reaction of β-chloro-β-(trifluoromethyl)styrenes with 2-iodophenols and 2-bromophenols.

Palladium-catalyzed tandem reaction of 2-hydroxyarylacetonitriles with sodium sulfinates: one-pot synthesis of 2-arylbenzofurans.

The first example of the palladium-catalyzed one-pot synthesis of 2-arylbenzofurans in moderate to excellent yields via a tandem reaction of 2-hydroxyarylacetonitriles with sodium sulfinates is reported. A plausible mechanism for the formation of 2-arylbenzofurans involving desulfinative addition and intramolecular annulation reactions is proposed. Moreover, the present synthetic route to benzofurans could be readily scaled up to the gram quantity without any difficulty. Thus, the method represents a convenient and practical strategy for synthesis of benzofuran derivatives.

Synthesis of 3-Trifluoromethylbenzofurans via Palladium-Catalyzed Tandem Elimination/Annulation of β-Chloro-β-(trifluoromethyl)styrenes with 2-Halophenols

A palladium-catalyzed tandem elimination and annulation reaction has been developed. In this way, a variety of 3-trifluoromethybenzofurans were prepared in moderate to good yields via tandem reaction of β-chloro-β-(trifluoromethyl)styrenes with 2-iodophenols and 2-bromophenols.

Palladium‐Catalyzed Skeletal Rearrangement of Spirotricyclic Olefins: A Facile One‐Pot Strategy for the Synthesis of a Novel Motif with Cyclopentene Fused to Benzofuran and Pyrazolidine

Complex molecule synthesis: An efficient one-pot strategy for the synthesis of a novel framework of benzofuran-pyrazolidine-fused cyclopentenes by a palladium-catalyzed tandem reaction of cyclopropane-bearing spirotricyclic olefins with 2-iodophenols is reported (see scheme).

ChemInform Abstract: Palladium‐Catalyzed Tandem Reaction of o‐Aminophenols, Bromoalkynes and Isocyanides to Give 4‐Amine‐benzo[b][1,4]oxazepines

Abstract32 examples

Generation of 6H-benzo[f]cyclopenta[d][1,2]thiazepine 5,5-dioxides via a palladium-catalyzed reaction of 2-(2-alkynyl)benzenesulfonamide

An efficient approach for the assembly of 6H-benzo[f]cyclopenta[d][1,2]thiazepine 5,5-dioxides via a palladium-catalyzed tandem reaction of 2-(2-alkynyl)benzenesulfonamide with 2-alkynylvinyl bromide is reported. This transformation proceeds smoothly through a double carbopalladation with high efficiency.

Facile assembly of cyclopenta[c]quinolin-3-ols via a palladium-catalyzed reaction of 2-alkynylaniline with 2-alkynylvinyl bromide

A palladium-catalyzed tandem reaction of 2-alkynylaniline with 2-alkynylvinyl bromide provides an efficient route for the assembly of cyclopenta[c]quinolin-3-ols. A double insertion of triple bonds is the key step during the transformation.

ChemInform Abstract: Generation of Cyclopenta[c]chromenes via a Palladium‐Catalyzed Reaction of 2‐Alkynylphenol with 2‐Alkynylvinyl Bromide.

A palladium-catalyzed tandem reaction of 2-alkynylphenol with 2-alkynylvinyl bromide gives rise to cyclopenta[c]chromenes in good yields. Three bonds are formed during the process and a double insertion of triple bonds is believed to be the key step.

ChemInform Abstract: Palladium‐Catalyzed Tandem Reactions of β‐(2‐Bromophenyl)‐α,β‐Unsaturated Carbonyl Compounds with 2‐Hydroxyphenylboronic Acid: A New Route to Benzo[c]chromenes.

Palladium-catalyzed tandem reactions of β-(2-bromophenyl)-α,β-unsaturated carbonyl compounds with 2-hydroxyphenylboronic acid for the synthesis of benzo[c]chromenes are presented. This mild reaction allows formation of onecarbon–carbon bond and one carbon–oxygen bond in one pot.

Generation of Indeno[1,2-c]pyrroles via a Pd-Catalyzed Reaction of 2-Alkynylbromobenzene with Propargylic Sulfonamide

A novel route for the efficient assembly of indeno[1,2-c]pyrrole derivatives via a palladium-catalyzed tandem reaction of 2-alkynylbromobenzene with propargylic sulfonamide is reported. The starting materials are easily available, and the reaction proceeds smoothly with good functional group tolerance.

Palladium-catalyzed tandem reaction of o-aminophenols, bromoalkynes and isocyanides to give 4-amine-benzo[b][1,4]oxazepines

A robust route to 4-amine-benzo[b][1,4]oxazepines relying upon a palladium-catalyzed tandem reaction of o-aminophenols, bromoalkynes and isocyanides has been developed. This chemistry presumably proceeds through the migratory insertion of isocyanides into the vinyl-palladium intermediate as a key step.

Generation of cyclopenta[c]chromenes via a palladium-catalyzed reaction of 2-alkynylphenol with 2-alkynylvinyl bromide

A palladium-catalyzed tandem reaction of 2-alkynylphenol with 2-alkynylvinyl bromide gives rise to cyclopenta[c]chromenes in good yields. Three bonds are formed during the process and a double insertion of triple bonds is believed to be the key step.

Direct and mild palladium-catalyzed aerobic oxidative synthesis of imines from alcohols and amines under ambient conditions

By ligand, TEMPO, and base screening, we developed a mild and green one-pot imine synthesis from alcohols and amines via a low-loading palladium-catalyzed tandem aerobic alcohol oxidation-dehydrative condensation reaction that can be readily carried out in open air at room temperature.

Palladium-catalyzed tandem reaction to construct benzo[c]phenanthridine: application to the total synthesis of benzo[c]phenanthridine alkaloids

A concise and efficient synthesis of benzo[c]phenanthridines was accomplished by the palladium-catalyzed ring-opening coupling of azabicyclic alkene with o-iodobenzoates, followed by tandem cyclization. The strategy was successfully applied in the total synthesis of benzo[c]phenanthridine alkaloids such as sanguinarine, chelerythrine, nitidine and avicine.

Palladium-catalyzed reaction of 2-alkynylhalobenzene with 2-alkynylbenzamide: an efficient approach to indeno[1,2-c]azepin-3(2H)-ones

A novel and efficient route for rapid access to indeno[1,2-c]azepin-3(2H)-ones is described, which proceeds through a palladium-catalyzed tandem reaction of 2-alkynylhalobenzene with 2-alkynylbenzamide in the presence of PPh(3) or PCy(3). The indeno[1,2-c]azepin-3(2H)-ones which incorporate both indene and unsaturated seven-membered ring lactam skeletons are obtained in good to excellent yields.