Abstract
A concise and efficient cross-coupling synthetic strategy has been developed to construct 2-aryl-4H-thiochromen-4-one derivatives from 2-sulfinyl-thiochromones and arylboronic acids. This reaction proceeds via a catalyst system of Lewis acid and palladium(II) combined with XPhos as an optimal ligand in moderate to good yields. Besides, this flexible methodology provides a wide scope for the synthesis of different functionally substituted thiochromone scaffolds and can be further exploited to construct diverse thioflavone libraries for pharmaceutical research.
Highlights
Thioflavones are an important class of sulfur-containing heterocycles in medicinal chemistry due to their structural similarity to flavones, and this scaffold exhibits various biological and pharmacological properties,[1] including antibacterial,[2,3] anticancer,[4−6] and anti-HIV activities.[7]
2-(methylsulfinyl)-4H-thiochromen-4-one (1a), which was synthesized according to the reported method,[24] and phenylboronic acid (2a) were chosen as the test substrates for the reaction in the presence of Pd(OAc)[2] to investigate the feasibility of our method
To the best of our knowledge, this is the first use of sulfinyls as coupling partners to construct thioflavones through an organoboron crosscoupling reaction
Summary
Thioflavones are an important class of sulfur-containing heterocycles in medicinal chemistry due to their structural similarity to flavones, and this scaffold exhibits various biological and pharmacological properties,[1] including antibacterial,[2,3] anticancer,[4−6] and anti-HIV activities.[7] the synthetic methods for thioflavones via cross-coupling reaction are rarely reported. To the best of our knowledge, there are no reports of the construction of thioflavones via cross-coupling reactions using sulfinyls as coupling partners. Organoboron-mediated cross-coupling is a useful C−C bond-forming reaction. Flavones can be synthesized by organoboron crosscoupling;[20,21] especially, the synthesis of flavones via transition metal-catalyzed cross-coupling reactions has attracted our attention.[22,23]
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