21036-63-5Relevant articles and documents
Predictable and site-selective functionalization of poly(hetero)arene compounds by palladium catalysis
Lapointe, David,Markiewicz, Thomas,Whipp, Christopher J.,Toderian, Amy,Fagnou, Keith
supporting information; experimental part, p. 749 - 759 (2011/04/16)
The challenge of achieving selective and predictable functionalizations at C-H bonds with complex poly(hetero)aromatic substrates was addressed by two different approaches. Site-selectivity can be obtained by applying various reaction conditions that are (hetero)arene specific to substrates that contain indoles, pyridine N-oxide, and polyfluorinated benzenes. An experimental classification of electron-rich heteroarenes based on their reactivity toward palladium-catalyzed C-Hfunctionalization was established, the result of which correlated well with the order of reactivity predicted by the DFT-calculated concerted metalation-deprotonation (CMD) pathway. Model substrates containing two reactive heteroarenes were then reacted under general reaction conditions to demonstrate the applicability this reactivity chart in predicting the regioselectivity of the palladium-catalyzed direct arylation and benzylation reactions.
A convenient synthesis of 4-(2-furyl)-2-substituted thiazoles utilising [hydroxy(tosyloxy)iodo]benzene
Singh, Shiv P.,Naithani, Rajesh,Aggarwal, Ranjana,Prakash, Om
, p. 2371 - 2378 (2007/10/03)
A facile synthesis of 4-(2-furyl)-2-substituted thiazoles by hypervalent iodine oxidation of 2-acetylfuran (1) using [hydroxy(tosyloxy)iodo]benzene, followed by treatment of the reaction mixture with appropriate thioureas/thioamides is described.
