Tan et al.
Report
Interactions Listed in Drug Monographs. J Am Pharm Assoc 2017, 57,
Feng, M.; Jiang, X. New Design of Disulfurating Reagent: Facile and
Straightforward Pathway to Unsymmetrical Disulfanes via
Cu-Catalyzed Oxidative Cross Coupling. Angew. Chem. Int. Ed. 2016,
55, 14121-14125. (k) Li, Y.; Wang, M.; Jiang, X. Controllable
Sulfoxidation and Sulfenylation with Organic Thiosulfate Salts via
Dual Electron- and Energy-Transfer Photocatalysis. ACS Catal. 2017, 7,
7587-7592. (l) Xiao, X.; Xue, J.; Jiang, X.; Polysulfurating Reagent
Design for Unsymmetrical Polysulfide Construction. Nat. Commun.
2018, 9, 2191. (m) Chen, S.; Wang, M.; Jiang, X. Pd-Catalyzed C-S
Cyclization via C-H Functionalization Strategy: Access to
Sulfur-containing Benzoheterocyclics. Chin. J. Chem. 2018, 36,
921-924. (n) Wang, M.; Dai, Z.; Jiang, X. Design and application of
α-ketothioesters as 1,2-dicarbonyl-forming reagents. Nat. Commun.
2019‚ 10‚ 2661. (o) Li, Y.; Rizvi, S. A.; Hu, D.; Sun, D.; Gao, A.; Zhou, Y.;
Li, J.; Jiang, X. Selective Late-Stage Oxygenation of Sulfides with
Ground-State Oxygen by Uranyl Photocatalysis. Angew. Chem. Int. Ed.
2019, 58, DOI: 10.1002/anie.201906080.
698-703. (c) Angehrn, P.; Goetschi, E.; Gmuender, H.; Hebeisen, P.;
Hennig, M.; Kuhn, B.; Luebbers, T.; Reindl, P.; Ricklin, F.;
Schmitt-Hoffmann, A. A New DNA Gyrase Inhibitor Subclass of the
Cyclothialidine Family Based on a Bicyclic Dilactam-Lactone Scaffold.
Synthesis and Antibacterial Properties. J. Med. Chem. 2011, 54,
2207-2224.
(a) Hermant, F.; Urbańska, E.; Mazancourt, S. S.; Maubert, T.; Nicolas,
E.; Six, Y. Reductive Alkylation of Thioamides with Grignard Reagents
in the Presence of Ti(OiPr)4: Insight and Extension. Organometallics
2014, 33, 5643−5653. (b) Augustowska, E.; Boiron, A.; Deffit, J.; Six, Y.
Kulinkovich-type Reactions of Thioamides: Similar to Those of
Carboxylic Amides. Chem. Commun. 2012, 48, 5031–5033.
Neto, B. A. D.; Lapis, A. A.M.; Bernd, A. B.; Russowsky, D. Studies on
the Eschenmoser Coupling Reaction and Insights on Its Mechanism.
Application in the Synthesis of Norallosedamine and Other Alkaloids.
Tetrahedron 2009, 65, 2484–2496.
(a) Wang, N.; Du, S.; Li, D.; Jiang, X. Divergent Asymmetric Total
(a) Wei, J.; Li, Y.; Jiang, X. Aqueous Compatible Protocol to Both Alkyl
and Aryl Thioamide Synthesis. Org. Lett. 2016, 18, 340-343. (b) Tan,
W.; Wei, J.; Jiang, X. Thiocarbonyl Surrogate via Combination of
Sulfur and Chloroform for Thiocarbamide and Oxazolidinethione
Constructions. Org. Lett. 2017, 19, 2166-2169. (c) Tan, W.; Wang, C.;
Jiang, X. Green Carbon Disulfide Surrogate via Combination of
Potassium Sulfide and Chloroform for Benzothiazine-thione and
Benzothiazole-thione Constructions. Org. Chem. Front. 2018, 5,
2390-2394.
Synthesis
of
(+)-Vincadifformine,
(−)-Quebrachamine,
(+)-Aspidospermidine, (−)-Aspidospermine, (−)-Pyrifolidine, and
Related Natural Products. Org. Lett. 2017, 19, 3167-3170. (b) Wang,
N.; Liu, J.; Wang, C.; Bai, L.; Jiang, X. Asymmetric Total Syntheses of
(−)-Jerantinines A, C, and E, (−)-16-Methoxytabersonine,
(−)-Vindoline, and (+)-Vinblastine. Org. Lett. 2018, 20, 292−295.
(a) Ozturk, T.; Ertas, E.; Mert, O. Use of Lawesson's Reagent in
Organic Syntheses. Chem. Rev. 2007, 107, 5210. (b) Ozturk, T.; Ertas,
E.; Mert, O. A Berzelius Reagent, Phosphorus Decasulfide (P4S10), in
Organic Syntheses. Chem. Rev. 2010, 110, 3419. (c) Baudin, J. B.;
Bekhazi, M.; Julia, S. A.; Ruel, O.; De Jong, R. L. P.; Brandsma, L.
Thermal Rearrangements of N-Aryl-1-alkynesulphenamides into
Indoline-2-thiones. Synthesis 1985, 10, 956-958. (d) Kaleta, Z.;
Tárkányi, G.; Gömöry, Á.; Kálmán, F.; Nagy, T.; Soós, T. Synthesis and
Reviews: (a) Beatty, J. W.; Stephenson, C. R. J. Amine
Functionalization via Oxidative Photoredox Catalysis: Methodology
Development and Complex Molecule Synthesis. Acc. Chem. Res. 2015,
48, 1474−1484. (b) Hu, J.; Wang, J.; Nguyen, T. H.; Zheng, N. The
Chemistry of Amine Radical Cations Produced by Visible Light
Photoredox Catalysis. Beilstein J. Org. Chem. 2013, 9, 1977–2001. For
selected examples: (c) Miyake, Y.; Nakajima, K.; Nishibayashi, Y.
Visible-Light-Mediated Utilization of α-Aminoalkyl Radicals: Addition
to Electron-Deficient Alkenes Using Photoredox Catalysts. J. Am.
Chem. Soc. 2012, 134, 3338−3341. (d) Le, C.; Liang, Y.; Evans, R. W.; Li,
X.; MacMillan, D. W. C. Selective sp3 C–H Alkylation via
Polarity-match-based Cross-coupling. Nature, 2017, 547, 79–83. (e)
Bartling, H.; Eisenhofer, A.; König, B.; Gschwind, R. M. The
Photocatalyzed Aza-Henry Reaction of N-Aryltetrahydroisoquinolines:
Comprehensive Mechanism, H•-versus H+-Abstraction, and
Background Reactions. J. Am. Chem. Soc. 2016, 138, 11860−11871.
Reviews: (a) Chivers, T.; Elder, P. J. W. Ubiquitous Trisulfur Radical
Anion: Fundamentals and Applications in Materials Science,
Electrochemistry, Analytical Chemistry and Geochemistry. Chem. Soc.
Rev. 2013, 42, 5996-6005. (b) Steudel, R.; Chivers, T. The role of
polysulfide dianions and radical anions in the chemical, physical and
biological sciences, including sulfur-based batteries. Chem. Soc. Rev.
2019, 10.1039/c8cs00826d. For selected examples: (c) Zhang, G.; Yi,
H.; Chen, H.; Bian, C.; Liu, C.; Lei, A. Trisulfur Radical Anion as the Key
Intermediate for the Synthesis of Thiophene via the Interaction
between Elemental Sulfur and NaOtBu. Org. Lett. 2014, 16, 6156–
6159. (d) Gu, Z. Y.; Cao, J. J.; Wang, S. Y.; Ji, S. J. The Involvement of
the Trisulfur Radical Anion in Electron-catalyzed Sulfur Insertion
Reactions: Facile Synthesis of Benzothiazine Derivatives under
Transition Metal-free Conditions. Chem. Sci. 2016, 7, 4067-4072. (e)
Application of
a Fluorous Lawesson's Reagent:ꢀ Convenient
Chromatography-Free Product Purification. Org. Lett. 2006, 8, 1093–
1095. (e) Lacroix, S.; Rixhon, V.; Marchand-Brynaert, J. Synthesis of
ω-Aminodithioesters. Synthesis 2006, 14, 2327-2334.
Reviews: (a) Liu, H.; Jiang, X. Transfer of Sulfur: From Simple to
Diverse. Chem. Asian J. 2013, 8, 2546-2563. (b) Feng, M.; Tang, B.;
Liang, S.; Jiang, X. Sulfur Containing Scaffolds in Drugs: Synthesis and
Application in Medicinal Chemistry. Curr. Top. Med. Chem. 2016, 16,
1200-1216. (c) Jiang, X. Sulfur Atom Transfer (SAT) Reaction.
Phosphorus, Sulfur Silicon Relat. Elem. 2017, 192, 169-171. (d) Qiao,
Z.; Jiang, X. Recent Developments in Sulfur-Carbon Bond Formation
Reaction Involving Thiosulfates. Org. Biomol. Chem. 2017‚ 15,
1942-1946. (e) Wang, Y.; Li, Y.; Jiang, X. Sulfur-Center-Involved
Photocatalyzed Reaction. Chem. Asian J. 2018, 13, 2208-2242. (f)
Wang, M.; Jiang, X. Sulfur-Sulfur Bond Construction. Top. Curr. Chem.
2018, 376, 14. For representative examples: (g) Qiao, Z.; Wei, J.;
Jiang, X. Direct Cross-Coupling Access to Diverse Aromatic Sulfide:
Palladium-Catalyzed Double C−S Bond Construction Using Na2S2O3 as
a Sulfurating Reagent. Org. Lett. 2014, 16, 1212-1215. (h) Li, Y.; Xie,
W.; Jiang, X. Mechanistic Study of a Photocatalyzed C-S Bond
Formation Involving Alkyl/Aryl Thiosulfate. Chem. Eur. J. 2015, 21,
16059-16065. (i) Qiao, Z.; Jiang, X. Ligand Controlled Divergent
Cross-Coupling Involving Organosilicon Compounds for Thioether
and ThioesterSynthesis. Org. Lett. 2016, 18, 1550-1553. (j) Xiao, X.;
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