Aqueous protocol for allylic arylation of cinnamyl acetates with sodium tetraphenylborate using a Bedford-type palladacycle catalyst

Ghorpade, Seema; Sawant, Dinesh N.; Renn, Dominik; Zernickel, Anna; Du, Weiyuan; Sekar, Nagaiyan; Eppinger, Jörg

doi:10.1039/c8nj00660a

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Cited by 9 publications

References 83 publications

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Recent Advances in Organic Reactions Using Water as Solvent

Wang,

Sun,

Wang

et al. 2024

Green Solvents in Organic Synthesis

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Recent Advances in Organic Reactions Using Water as Solvent

Wang,

Sun,

Wang

et al. 2024

Green Solvents in Organic Synthesis

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Friedel−Crafts‐Type Allylation of Phenol Derivatives Catalyzed by In Situ‐Generated Silyl Cyanometallates

2020

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We successfully demonstrated that Friedel−Crafts‐type allylation of phenol derivatives and allylic phosphates is catalyzed by the AgTFA/trimethylsilyl cyanide (Me3SiCN) and Pd(OAc)2/Me3SiCN combined systems to afford the C‐allylated product in a highly regioselective manner. The corresponding silyl cyanometallates generated in situ are proposed to be the active catalytic species. Lewis acidity of the reversibly formed ion pairs is appropriately regulated for this reaction. The para‐allylated anisole and phenol derivatives are selectively obtained. The para‐substituted ones are converted to the ortho‐allylated products. The reactivity of the catalytic systems is strongly dependent on the electronic nature of both electrophile and nucleophile. Substitution of an aromatic ring on the allylic phosphate is essential for the reaction. Thus, the competitive reaction of a 1 : 1 mixture of cinnamyl and simple allyl phosphates affords only the cinnamyl‐substituted product.

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Enantioselective Nickel‐Catalyzed Hydrocyanation of Homostilbenes

et al. 2023

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We investigated the previously unknown enantioselective Nicatalyzed hydrocyanation of 1,3-diarylpropenes (homostilbenes). For this purpose, a series of (E)-homostilbenes were prepared by (microwave-assisted) Pd-catalyzed coupling of allylic alcohols with aryl-boronic acids. Employing our established catalyst system formed from Ni(cod) 2 and a TADDOLderived chiral phosphine-phosphite ligand and using TMSCN as an in situ source of HCN, the hydrocyanation of various homostilbenes was studied. The synthetic usefulness of the methodology was demonstrated in a short synthesis of the new (allo-) colchicine analogue 7-cyano-11-methoxy-colchinol involving an PIDA-mediated oxidative cyclization of the corresponding hydrocyanation product to set up the 7-membered ring. The absolute configuration of 2,4-diphenylbutyronitrile was assigned by comparison of experimental and calculated ECD spectra.

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Aqueous protocol for allylic arylation of cinnamyl acetates with sodium tetraphenylborate using a Bedford-type palladacycle catalyst

Abstract: Allylic arylation using 0.002 mol% of a Bedford-type palladacycle catalyst is described under mild reaction conditions.

Cited by 9 publications

References 83 publications

Recent Advances in Organic Reactions Using Water as Solvent

Recent Advances in Organic Reactions Using Water as Solvent

Friedel−Crafts‐Type Allylation of Phenol Derivatives Catalyzed by In Situ‐Generated Silyl Cyanometallates

Enantioselective Nickel‐Catalyzed Hydrocyanation of Homostilbenes

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