15185-05-4Relevant articles and documents
Rh(I)-catalyzed cross-coupling reactions of alkenyl tosylates with potassium aryltrifluoroborates
Wu, Jie,Zhang, Liang,Luo, Yong
, p. 6747 - 6750 (2006)
RhCl(PPh3)3/DPPF was successfully employed as an efficient catalyst in the Suzuki-Miyaura cross-coupling reactions of potassium aryltrifluoroborates with alkenyl tosylates, affording the corresponding products in good to excellent yi
Magnesium bis(trifluoromethane)sulfonimide: An efficient catalyst for the synthesis of coumarins under solvent-free conditions
Wang, Hongshe
, p. 411 - 414 (2013)
Magnesium bis(trifluoromethane)sulfonimide [Mg(NTf2) 2] is an efficient catalyst for the synthesis of coumarins via the Pechmann condensation reaction of phenols and β-ketoesters under solvent-free conditions.
An evaluation of palladium-based catalysts for the base-free borylation of alkenyl carboxylates
Gaube, Gregory,Leitch, David C.,Pipaon Fernandez, Nahiane
, p. 20095 - 20098 (2021/11/22)
Synthesis of organoboron derivatives is a key application of catalytic cross-coupling, with the Pd-catalyzed Miyaura borylation among the most versatile methods available. We have evaluated several Pd-based systems for borylation of alkenyl acetates and p
Coumarins by Direct Annulation: β-Borylacrylates as Ambiphilic C3-Synthons
Wienhold, Max,Molloy, John J.,Daniliuc, Constantin G.,Gilmour, Ryan
, p. 685 - 689 (2020/11/30)
Modular β-borylacrylates have been validated as programmable, ambiphilic C3-synthons in the cascade annulation of 2-halo-phenol derivatives to generate structurally and electronically diverse coumarins. Key to this [3+3] disconnection is the BPin unit which serves a dual purpose as both a traceless linker for C(sp2)–C(sp2) coupling, and as a chromophore extension to enable inversion of the alkene geometry via selective energy transfer catalysis. Mild isomerisation is a pre-condition to access 3-substituted coumarins and provides a handle for divergence. The method is showcased in the synthesis of representative natural products that contain this venerable chemotype. Facile entry into π-expanded estrone derivatives modified at the A-ring is disclosed to demonstrate the potential of the method in bioassay development or in drug repurposing.