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Palladium-Catalyzed Dual-Tasked -C-H Borylation of Aryl Iodides.
Org Lett
December 2024
School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University, Shanghai 200092, People's Republic of China.
Article Synopsis
- A new method has been developed for Pd-catalyzed C-H borylation using maleimide to activate C-H bonds in aryl iodides.
- This reaction allows for the alkylation of -positions and borylation of -C-H bonds, leading to the synthesis of functionalized 3-aryl succinimides, which are important in various organic compounds.
- The boronate group created in this process can be further modified, showcasing the practical applications and potential of this C-H activation strategy for difunctionalizing aryl halides.
Stereo- and Enantioselective Syntheses of 1,2-Oxaborinan-3-enes and δ-Boryl-Substituted Homoallylic Alcohols.
Org Lett
November 2024
Department of Chemistry, Virginia Tech, Blacksburg, Virginia 24061, United States.
Stereo- and enantioselective syntheses of 1,2-oxaborinan-3-enes and δ-boryl-substituted homoallylic alcohols are reported. We developed a practical approach to synthesize α-boryl-substituted allylboronate. This reagent was utilized to generate α,α-disubstituted allylboronates, and such reagents cannot be accessed via the Pd-catalyzed alkene isomerization approach.
View Article and Find Full Text PDFSynthesis of Biheteroaryls by Pd-Catalyzed Homocoupling of Heteroaryl Bromides.
Org Lett
October 2024
State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, China.
Symmetrical biheteroaryl compounds, such as bypyridines and bipyrazoles, are important ligands in transition-metal catalysis. They also serve as synthetic precursors of photo catalysts/sensitizers, bioactive agents, and energetic materials. To facilitate the concise synthesis of these useful structures, an efficient Pd-catalyzed homocoupling of heteroaryl bromides has been successfully established using the electron-rich and sterically hindered monophosphorus ligand BIDIME.
View Article and Find Full Text PDFPd-Catalyzed Borylation in Water and Its Application to the Synthesis of Active Pharmaceutical Ingredient (API) Intermediates.
J Org Chem
September 2024
Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca' Foscari di Venezia, Via Torino 155, Mestre, 30172 Venezia, Italy.
An efficient catalytic borylation reaction of aryl bromides in water based on Pd catalysis under micellar conditions is presented. The peculiar combination of the proper Pd precursor with a Sphos ligand and a hindered lipophilic base ensures good yields in the synthesis of a wide range of boronic esters, even for heteroaryl derivatives with a good purity profile. The method is specifically developed for the preparation of boronic esters that are directly converted into examples of relevant active pharmaceutical ingredient intermediates through cross-coupling reactions or via oxidation to phenols.
View Article and Find Full Text PDFSynthesis of Tanshinone IIA and Related Terpenes via a C-H Functionalization Strategy.
Org Lett
August 2024
Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland A1B 3X7, Canada.
Article Synopsis
- The total synthesis of tanshinone IIA, a bioactive diterpene from a Chinese plant, was achieved using a common tetralin building block.
- Key methods in the synthesis included creating a 3,4-disubstituted furan and employing regioselective C-H functionalization reactions, like Pd-catalyzed iodination and Ir-catalyzed borylation.
- An intramolecular stanna-Brook type reaction was utilized to build the quinone ring structure of the target compound.
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