Tandem Aryl Research Articles

Aryl Ketone Synthesis via Tandem Orthoplatinated Triarylphosphite-Catalyzed Addition Reactions of Arylboronic Acids with Aldehydes Followed by Oxidation

Tandem orthoplatinated triaryl phosphite-catalyzed addition reactions of arylboronic acids with aldehydes followed by oxidation to yield aryl ketones is described. 3-Pentanone was identified as a suitable oxidant for the tandem aryl ketone formation reaction. By using microwave energy, aryl ketones were obtained in high yields with the catalyst loading as low as 0.01%.

Palladium‐Catalyzed Highly Stereoselective Synthesis of N‐Aryl‐3‐arylmethylisoxazolidines via Tandem Arylation of O‐Homoallylhydroxylamines.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Synthesis of Tricyclic Heterocycles via a Tandem Aryl Alkylation/Heck Coupling Sequence.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Palladium-Catalyzed Highly Stereoselective Synthesis of N-Aryl-3-arylmethylisoxazolidines via Tandem Arylation of O-Homoallylhydroxylamines

The palladium-catalyzed tandem arylation of O-homoallylhydroxylamines with 2 equiv of aryl bromides was examined. With Pd2(dba)3 (1 mol %) as the catalyst, Xantphos (2 mol %) as the ligand, and NaOt-Bu as the base, the reactions of O-homoallylhydroxylamines with aryl bromides via sequential N-arylation/cyclization/C-arylation in toluene afforded the corresponding N-aryl-3-arylmethylisoxazolidines in good yields with excellent diastereoselectivity.

Synthesis of Tricyclic Heterocycles via a Tandem Aryl Alkylation/Heck Coupling Sequence

A norbornene-mediated palladium-catalyzed sequence is described in which two alkyl-aryl bonds and one alkenyl-aryl bond are formed in one pot with use of microwave irradiation. A variety of symmetrical and unsymmetrical oxygen-, nitrogen-, silicon-, and sulfur-containing tricyclic heterocycles were synthesized from a Heck acceptor and an aryl iodide containing two tethered alkyl halides. This approach was further applied to the synthesis of a tricyclic mescaline analogue.

Pd‐Catalyzed Selective Tandem Arylation—Alkylation of 1,1‐Dihalo‐1‐alkenes with Aryl‐ and Alkylzinc Derivatives to Produce α‐Alkyl‐substituted Styrene Derivatives.

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Pd-catalyzed selective tandem arylation–alkylation of 1,1-dihalo-1-alkenes with aryl- and alkylzinc derivatives to produce α-alkyl-substituted styrene derivatives

Trans-selective monoarylation of 1,1-dibromo- and 1,1-dichloro-1-alkenes ( 1) can be achieved in >80% yields and in ≥98–99% stereoselectivity with arylzinc bromides in the presence of a catalytic amount of Cl 2Pd(DPEphos) or Cl 2Pd(dppb), the former permitting cleaner and higher yielding reactions. Although THF is a generally satisfactory solvent, ether and toluene are superior to THF in some cases. The second substitution of ( Z)-α-bromostyrenes ( 3) with alkylzincs in the presence of 2 mol% of Pd( t Bu 3P) 2 proceeds to give the corresponding 2 in >90% yields and in ≥98–99% stereoselectivity. Although somewhat less satisfactory, the use of Cl 2Pd(DPEphos) permits a one-pot tandem arylation–alkylation.