Addition of arylboronic acids to directing group tethered acetylenes in a regio and stereoselective manner using an inexpensive catalytic system is achieved for the first time to access highly sought after allyl/homoallyl alcohol/amine units. The apparent vinylnickel intermediate was successfully trapped by the Michael electrophiles to get defined tri- and tetra-substituted olefins. An interesting selectivity switch was observed with internal alkynes.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1039/c6cc10256e | DOI Listing |
J Org Chem
December 2024
Department of Chemistry, Jadavpur University, Kolkata 700032, India.
We have developed a novel protocol for carbonylative homocoupling of arylboronic acids using dithiocarbamate esters as the carbonyl alternative. A series of arylboronic acids underwent smooth reaction with dithiocarbamate ester (MeNCSMe) in the presence of Pd(PPh)Cl catalyst, Cu(OAc)·HO additive, and NaCO in DCE solvent, producing the biaryl ketones efficiently. The mechanism has been studied with the help of several control experiments that reveal the probability of thioamide intermediacy.
View Article and Find Full Text PDFJ Org Chem
December 2024
College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China.
Nat Commun
November 2024
Engineering Research Center of Sichuan-Tibet Traditional Medicinal Plant, College of Chemistry and Chemical Engineering, Chengdu University, Chengdu, China.
Carbon-silicon-switch strategy, replacing one specific carbon atom in organic molecules with a silicon, has garnered significant interest for developing new functional molecules. However, the influence of a reaction regarding its selectivity and reactivity by carbon-silicon-switch strategy has far less been investigated. Here we discover an unusual carbon-silicon-switch effect in the enantioselective construction of silicon-stereogenic center.
View Article and Find Full Text PDFNat Commun
October 2024
Inner Mongolia Key Laboratory of Fine Organic Synthesis, Inner Mongolia University, 235 West University Street, Hohhot, 010021, China.
ChemistryOpen
December 2024
Leibniz Universität Hannover, Institut für Organische Chemie, Schneiderberg 1B, D-30167, Hannover, Germany.
A number of new deoxyvasicinone (2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one) and mackinazolinone (6,7,8,9-tetrahydro-11H-pyrido[2,1-b]quinazolin-11-one) derivatives with aryl substituents at C7/C8 and at C5 are reported. These compounds are rare representatives of their kind and were prepared in high yields by Suzuki-Miyaura cross-coupling reactions between 7-bromo-2,3-dihydro[2,1-b]quinazoline-9-(1H)-one, 5,7-dibromo-2,3-dihydro[2,1-b]quinazoline-9-(1H)-one or 8-bromomackinazolinone and respective arylboronic acids with palladium acetate as the catalyst. The products were characterized spectroscopically and, in addition, by X-ray crystal structure analyses in six cases.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!