107793-07-7Relevant articles and documents
Improved procedures for the palladium-catalyzed coupling of terminal alkynes with aryl bromides (Sonogashira coupling)
Thorand,Krause
, p. 8551 - 8553 (1998)
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Palladium cross-coupling reactions on solid support using a new silylated linker
Duboc, Romain,Savignac, Monique,Genêt, Jean-Pierre
, p. 512 - 515 (2002)
The synthesis and the use in palladium cross-coupling reactions of a new silylated stable resin were described. The products have been cleaved from the support using mild conditions and purified with a scavenger ionic resin. A small library of coupling pr
Cyclopentadienones as intermediates for the synthesis of highly functionalized biaryls
Pearson, Anthony J.,Kim, Jin Bum
, p. 8525 - 8527 (2003)
A new approach to the synthesis of substituted biaryls, via Diels-Alder reaction between cyclopentadienones and arylacetylenes, is described.
Cys–Cys and Cys–Lys Stapling of Unprotected Peptides Enabled by Hypervalent Iodine Reagents
Ceballos, Javier,Grinhagena, Elija,Sangouard, Gontran,Heinis, Christian,Waser, Jerome
, p. 9022 - 9031 (2021)
Easy access to a wide range of structurally diverse stapled peptides is crucial for the development of inhibitors of protein-protein interactions. Herein, we report bis-functional hypervalent iodine reagents for two-component cysteine-cysteine and cysteine-lysine stapling yielding structurally diverse thioalkyne linkers. This stapling method works with unprotected natural amino acid residues and does not require pre-functionalization or metal catalysis. The products are stable to purification and isolation. Post-stapling modification can be accessed via amidation of an activated ester, or via cycloaddition onto the formed thioalkyne group. Increased helicity and binding affinity to MDM2 was obtained for a i,i+7 stapled peptide.
Triflic acid mediated sequential cyclization of ortho-alkynylarylesters with ammonium acetate
Domaradzki, Maciej E.,Liu, Xiaochen,Ong, Jiye,Yu, Gyeongah,Zhang, Gan,Simantov, Ariel,Perl, Eliyahu,Chen, Yu
, (2020/08/03)
A triflic acid (TfOH) mediated sequential cyclization of ortho-alkynylarylesters and ammonium acetate (NH4OAc) was reported. The reaction took place via a Br?nsted acid-mediated intramolecular cyclization of ortho-alkynylarylesters followed by an ammonium acetate participated substitution reaction, forming isoquinolin-1-ones as the major products. Different from most of the known synthetic methods of isoquinolin-1-ones, no metal catalyst was required in the reported reaction. The regioisomers – isoindolin-1-ones were obtained together with isoquinolin-1-ones in a few cases. The intermediate compounds – isochromen-1-ones and isobenzofuran-1-ones were also isolated. The interconversion experiments showed that the regioisomers formed during the Br?nsted acid induced intramolecular cyclization of ortho-alkynylarylesters. A natural product – ruprechstyril was prepared in a moderate yield employing the new method.
Continuous Electrochemical Synthesis of Iso-Coumarin Derivatives from o-(1-Alkynyl) Benzoates under Metal- and Oxidant-Free
Lin, Xinxin,Fang, Zheng,Zeng, Cuilian,Zhu, Chenlong,Pang, Xinyan,Liu, Chengkou,He, Wei,Duan, Jindian,Qin, Ning,Guo, Kai
supporting information, p. 13738 - 13742 (2020/10/02)
A non-oxidant and metal-free strategy for synthesizing iso-coumarin by using a continuous electrochemical microreactor to initiate an oxidative cyclization reaction of o-(1-alkynyl) benzoate and radicals. This efficient and clean continuous electrosynthesis method not only avoids the complicated gas protection operation and production of by-products in the batch processes, but also help to overcome the difficulty that batch metal catalysis and electrocatalysis are difficult to scale up, and has the potential for pilot-scale experiment.
