Palladium-Catalyzed Addition Of Arylboronic Acids Research Articles

Kinetic Resolution of [2.2]Paracyclophane-Derived Cyclic N-Sulfonylimines via Palladium-Catalyzed Addition of Arylboronic Acids.

A facile method for kinetic resolution of [2.2]paracyclophane-derived cyclic N-sulfonylimines based on palladium-catalyzed addition of arylboronic acids was developed, giving two kinds of planar chiral [2.2]paracyclophane derivatives in excellent diastereoselectivities and up to 99% of enantioselectivities with high selectivity factors (s up to 128).

2-Arylpiperidines by Palladium-Catalyzed Addition of Arylboronic Acids to Acylated 2-Hydroxypiperidines

Key words arylpiperidines - aza-Achmatowicz reaction - palladium catalysis - arylboronic acids - hydroxypiperidines

Synthesis of chiral seven-membered cyclic sulfonamides through palladium-catalyzed arylation of cyclic imines

An enantioselective palladium-catalyzed addition of arylboronic acids to seven-membered cyclic N-sulfonyl aldimines and ketimines has been developed, giving the chiral cyclic sulfonamides with excellent yields and up to 99% ee.

Synthesis of paracyclophanes with planar and central chirality: kinetic resolution of [2.2]paracyclophane aldimines via palladium-catalyzed addition of arylboronic acids

Kinetic resolution of [2.2]paracyclophane aldimines was achieved through a palladium-catalyzed enantioselective arylation, providing access to chiral paracyclophanes with planar and central chirality as well as the recovered chiral aldimines.

Solvent control of product diversity in palladium-catalyzed addition of arylboronic acid to aryl aldehydes

In Pd-catalyzed arylboronic acid addition to aryl aldehydes, the expected carbinol or asymmetrical ether can be obtained as the major product by altering aqueous solvent composition. Exploiting this methodology with 2-formylbiphenyls as reaction partner, a fluorene scaffold can be readily constructed in two steps.

Total Synthesis of (–)-HM-3 and (–)-HM-4 Utilizing a Palladium-Catalyzed Addition of an Arylboronic Acid to an Allenic Alcohol Followed by Eschenmoser–Claisen Rearrangement

The first asymmetric total synthesis of (–)-HM-3 and (–)-HM-4, aromatic sesquiterpenes isolated from the phytopathogenic fungus Helicobasidium mompa, has been achieved. Highlight of the synthesis is an enantiospecific construction of the quaternary carbon stereocenter utilizing a palladium-catalyzed addition of arylboronic acid to the allenic alcohol followed by Eschenmoser–Claisen rearrangement.

ChemInform Abstract: Palladium‐Catalyzed Reaction of Arylboronic Acids with Aliphatic Nitriles: Synthesis of Alkyl Aryl Ketones and 2‐Arylbenzofurans.

An efficient palladium-catalyzed addition of arylboronic acids to aliphatic nitriles has been developed, providing a wide range of alkyl aryl ketones in moderate to excellent yields. It is noteworthy that sequential addition and intramolecular annulation reaction of 2-(2-hydroxyphenyl)acetonitriles with arylboronic acids are also conducted smoothly to afford 2-arylbenzofurans in good yields under the standard conditions.

ChemInform Abstract: A Palladium‐Catalyzed Enantioselective Addition of Arylboronic Acids to Cyclic Ketimines.

Sly as Nicox: A palladium-catalyzed addition of arylboronic acids to ketimines has been developed to efficiently provide products in up to 99 % yield and 96 % ee. The reactions could be run under aerobic conditions and with unpurified trifluoroethanol (TFE). A pyrrolidine compound bearing a chiral α-tertiary amine was synthesized in several steps without loss of enantioselectivity. TFA = trifluoroacetate.

Palladium-Catalyzed Reaction of Arylboronic Acids with Aliphatic Nitriles: Synthesis of Alkyl Aryl Ketones and 2-Arylbenzofurans

An efficient palladium-catalyzed addition of arylboronic acids to aliphatic nitriles has been developed, providing a wide range of alkyl aryl ketones in moderate to excellent yields. It is noteworthy that sequential addition and intramolecular annulation reaction of 2-(2-hydroxyphenyl)acetonitriles with arylboronic acids are also conducted smoothly to afford 2-arylbenzofurans in good yields under the standard conditions.

A Palladium‐Catalyzed Enantioselective Addition of Arylboronic Acids to Cyclic Ketimines

Sly as Nicox: A palladium-catalyzed addition of arylboronic acids to ketimines has been developed to efficiently provide products in up to 99 % yield and 96 % ee. The reactions could be run under aerobic conditions and with unpurified trifluoroethanol (TFE). A pyrrolidine compound bearing a chiral α-tertiary amine was synthesized in several steps without loss of enantioselectivity. TFA = trifluoroacetate.

Pd-catalyzed addition of boronic acids to vinylogous imines: a convenient approach to 3-sec-alkyl substituted indoles

A convenient approach to 3-sec-alkyl substituted indoles was developed via palladium-catalyzed addition of arylboronic acids to vinylogous imines generated in situ from sulfonylindoles under mild conditions.

Mechanism of the Palladium-Catalyzed Addition of Arylboronic Acids to Enones: A Computational Study

The palladium(II)-catalyzed addition of arylboronic acids to β,β-disubstituted enones has been investigated with the BP86 density functional. The results show that the mechanism requires three steps: transmetalation, alkene insertion, and protonation. The alkene insertion is the rate-determining step. For unactivated alkenes, the Heck-type β-hydride elimination is more favored than protonation.

Palladium-Catalyzed Cascade Aryl Addition/Intramolecular Lactonization of Phthalaldehyde To Access 3-Aryl- and Alkenylphthalides

A palladium-catalyzed addition of arylboronic acids to phthalaldehyde, followed by an intramolecular lactonization to access 3-substituted phthalides, is described. The procedure tolerates a series of functional groups, such as methoxyl, fluoro, chloro, and trifluoromethyl groups. It represents a procedure for the synthesis of 3-substituted phthalides.

Enantioselective formal total synthesis of aplysin utilizing a palladium-catalyzed addition of an arylboronic acid to an allenic alcohol—Eschenmoser/Claisen rearrangement

The enantioselective formal total synthesis of aplysin has been achieved utilizing a palladium-catalyzed addition of arylboronic acid to the allenic alcohol followed by the Eschenmoser/Claisen rearrangement as the key steps.

Palladium-catalyzed addition of arylboronic acids to isocyanates

The addition of arylboronic acids to isocyanates catalyzed by palladium acetate in the presence of triphenylphosphine as the ligand is described.

Palladium-Catalyzed Addition of Arylboronic Acids to N-Tosylarylimines

Pd-catalyzed addition of arylboronic acids to N-tosyl­arylimines was described by employing easily prepared, air-stable aminophosphine ligands, cheap inorganic base, and common organic solvents, providing diarylmethylamine derivatives through one-pot synthesis in moderate to good yields. The efficiency of this reaction was demonstrated by the compatibility with nitro, trifluoro­methyl, fluoro, chloro, and methoxy groups. Moreover, rigorous exclusion of air/moisture is not required in these transformations.

Palladium-Catalyzed Addition of Arylboronic Acids to Aldehydes

[reaction: see text] Arylboronic acids react with aldehydes in the presence of a base and a catalytic amount of a palladium(0) complex with chloroform, affording the corresponding secondary alcohols in good yields. General palladium complexes have no catalytic activity without chloroform. Chloroform is essential for this reaction, and palladium complex that was prepared from Pd(PPh3)4 with CHCl3 showed good catalytic acitivity as well.