While cycloaddition reactions of bicyclobutanes (BCBs) have emerged as a potent method for synthesizing (hetero-)bicyclo[.1.1]alkanes (usually ≤ 3), their utilization in the synthesis of bicyclo[4.1.1]octane derivatives (BCOs) is still underdeveloped. Here, a palladium-catalyzed formal (4 + 3) reaction of BCBs with 1,4-O/C dipole precursors for the synthesis of oxa-BCOs is described. Unlike previous catalytic polar (3 + X) cycloadditions of BCBs, which are typically achieved through the activation of BCB substrates, the current reaction represents a novel strategy for realizing the cycloaddition of BCBs through the activation of the "X" cycloaddition partner. Moreover, the obtained functionalized oxa-BCOs products can be readily modified through various synthetic transformations.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11317905 | PMC |
| http://dx.doi.org/10.1039/d4sc02998d | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Synthesis of Optically Active Spirocycles by a Sequence of Decarboxylative Asymmetric Allylic Alkylation and Heck Reaction.
Org Lett
December 2024
Institut für Chemie, Universität Oldenburg, D-26129 Oldenburg, Germany.
Optically active spirocycles were prepared in a sequence of two palladium-catalyzed reactions. In the first step, racemic α-(-iodophenyl)-β-oxo allyl esters were submitted to the palladium-catalyzed decarboxylative asymmetric allylic alkylation reaction, furnishing the α-allylated products with a quaternary stereocenter with good yields and enantioselectivities. Subsequently, these intermediate products were converted in a Heck reaction yielding the spirocyclic structures as a mixture of - and -cyclic regioisomers.
View Article and Find Full Text PDFPalladium-Catalyzed Ortho Alkoxylation of Oxazoline Derivatives: An Avenue to Reach Meta-Substituted Electron-Rich Arenes Exploiting Oxazoline as a Removeable Directing Group.
ACS Omega
November 2024
Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9/163, 1060 Vienna, Austria.
An efficient and highly regioselective palladium-catalyzed oxazoline-directed alkoxylation is reported. The reaction proceeds under air and mild temperatures (60 °C). A series of alcohols can be used as alkoxylating agents and concomitantly act as reaction solvents, whereas primary and secondary alcohols are tolerated.
View Article and Find Full Text PDFPalladium-catalyzed [3 + 2] cycloaddition of 4-vinyl-4-butyrolactones with sulfamate-derived cyclic imines: construction of sulfamate-fused pyrrolidines.
Org Biomol Chem
December 2024
Department of Chemistry and Innovation Center of Pesticide Research, China Agricultural University, Beijing 100193, P. R. China.
The palladium-catalyzed [3 + 2] decarboxylative cycloaddition of 4-vinyl-4-butyrolactones with sulfamate-derived cyclic imines has been developed, providing the sulfamate-fused pyrrolidine derivatives in high yields with good diastereoselectivities. The scale-up reaction and further derivation of the product worked well, demonstrating the potential application of the current reaction in organic synthesis. A plausible reaction mechanism was also proposed.
View Article and Find Full Text PDFPalladium-catalyzed C-H bond activation and decarboxylation for the assembly of indolo[1,2-]phenanthridine.
Org Biomol Chem
December 2024
Hubei Key Laboratory of Pollutant Analysis & Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi, Hubei 435002, People's Republic of China.
A direct and convenient strategy for the assembly of indolo[1,2-]phenanthridine a Pd-catalyzed tandem cyclization reaction is presented. The current strategy delivers a range of indolo[1,2-]phenanthridine derivatives by utilizing readily available 1-(2-iodophenyl)-1-indole and commercially available -bromobenzoic acids as the starting materials. The reaction features the formation of two C-C bonds through Pd-catalyzed C-H bond activation and decarboxylation.
View Article and Find Full Text PDFPalladium-Catalyzed Dearomative Heck/C(sp)-H Activation/Decarboxylative Cyclization of C2-Tethered Indoles.
Org Lett
November 2024
Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha, Hunan 410081, China.
Until now, palladium-catalyzed dearomative Heck reactions of indoles were largely limited to β-H elimination and nucleophilic capture of the transient alkyl-Pd(II) species. Herein, we disclose a novel palladium-catalyzed dearomative Heck/C(sp)-H activation/decarboxylative cyclization of C2-tethered indoles. In this protocol, the alkyl-Pd(II) species formed by dearomatization of C2-tethered indoles is not terminated by common β-H elimination or nucleophilic capture, but rather generates ,-palladacycle via C-H activation.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!