- Promoting Effect of Crystal Water Leading to Catalyst-Free Synthesis of Heteroaryl Thioether from Heteroaryl Chloride, Sodium Thiosulfate Pentahydrate, and Alcohol
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It is observed the crystal water in sodium thiosulfate pentahydrate (Na2S2O3·5H2O) can promote its multicomponent reaction with heteroaryl chlorides and alcohols, providing a facile, green, and specific synthesis of unsymmetrical heteroaryl thioethers via one-step formation of two C-S bonds under catalyst-, additive-, and solvent-free conditions. Mechanistic studies suggest that the crystal water in Na2S2O3·5H2O is crucial in generating the key thiol intermediates and byproduct NaHSO4, which then catalyzes the dehydrative substitution of alcohols with thiols to afford thioethers.
- Ma, Xiantao,Yu, Jing,Yan, Ran,Yan, Mengli,Xu, Qing
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p. 11294 - 11300
(2019/09/12)
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- Versatile C(sp2)?C(sp3) Ligand Couplings of Sulfoxides for the Enantioselective Synthesis of Diarylalkanes
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The reaction of chiral (hetero)aryl benzyl sulfoxides with Grignard reagents affords enantiomerically pure diarylalkanes in up to 98 % yield and greater than 99.5 % enantiomeric excess. This ligand coupling reaction is tolerant to multiple substitution patterns and provides access to diverse areas of chemical space in three operationally simple steps from commercially available reagents. This strategy provides orthogonal access to electron-deficient heteroaromatic compounds, which are traditionally synthesized by transition metal catalyzed cross-couplings, and circumvents common issues associated with proto-demetalation and β-hydride elimination.
- Dean, William M.,?iau?iulis, Mindaugas,Storr, Thomas E.,Lewis, William,Stockman, Robert A.
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supporting information
p. 10013 - 10016
(2016/08/16)
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- 2-pyrimidine Derivatives: New Bronchosecretolytic Agents
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2-pyrimidine derivatives (1a-n) promote the excretion of phenol red into the mouse trachea, indicating an increased tracheobronchial secretion.Furthermore, 2-pyrimidine (1a) (tasuldine) produces greater ex
- Schickaneder, Helmut,Engler, Heidrun,Szelenyi, Istvan
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p. 547 - 551
(2007/10/02)
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