Electrochemical Synthesis of Sultone Derivatives via Dehydrogenative C-O Bond Formation

被引：7

作者：

Mitsudo, Koichi ^{[1
]}

Okumura, Yasuyuki ^{[1
]}

Yohena, Kotaro ^{[1
]}

Kurimoto, Yuji ^{[1
]}

Sato, Eisuke ^{[1
]}

Suga, Seiji ^{[1
]}

机构：

[1] Okayama Univ, Grad Sch Nat Sci & Technol, Div Appl Chem, Okayama 7008530, Japan

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 19期

关键词：

RING-CLOSING METATHESIS; UNSATURATED SULTONES; SULFOCOUMARINS; INHIBITORS; ACCESS; ACIDS;

D O I：

10.1021/acs.orglett.3c01062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electrochemical dehydrogenative C-O bond formation for the synthesis of sultones was achieved. In the presence of K2CO3 and H2O, constant current electrolysis of [1,1 '-biphenyl]-2-sulfonyl chloride afforded an aryl-fused sultone quantitatively. Under the optimized conditions, a variety of sultone derivatives were obtained. Control experiments suggest that the electrochemical oxidation of the sulfonates generated in situ would afford sulfo radical intermediates.

引用

页码：3476 / 3481

页数：6

共 55 条

[1] Electroreductive Nickel-Catalyzed Thiolation: Efficient Cross-Electrophile Coupling for C-S Formation
Ang, Nate W. J.
Ackermann, Lutz
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (15) : 4883 - 4887
[2] Palladium-Catalysed Intramolecular Direct Arylation of 2-Bromobenzenesulfonic Acid Derivatives
Bheeter, Charles Beromeo
Bera, Jitendra K.
Doucet, Henri
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (18) : 3533 - 3538
[3] Electrochemically Induced Intermolecular Cross-Dehydrogenative C-O Coupling of β-Diketones and β-Ketoesters with Carboxylic Acids
Bityukov, Oleg V.
Matveeva, Olesya K.
Vil, Vera A.
Kokorekin, Vladimir A.
Nikishin, Gennady I.
Terent'ev, Alexander O.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (03) : 1448 - 1460
[4] From β-Amino-γ-sultone to Unusual Bicyclic Pyridine and Pyrazine Heterocyclic Systems: Synthesis and Cytostatic and Antiviral Activities
de Castro, Sonia
Familiar, Olga
Andrei, Graciela
Snoeck, Robert
Balzarini, Jan
Camarasa, Maria-Jose
Velazquez, Sonsoles
[J]. CHEMMEDCHEM, 2011, 6 (04) : 686 - 697
[5] 4-Benzyloxy-γ-Sultone Derivatives: Discovery of a Novel Family of Non-Nucleoside Inhibitors of Human Cytomegalovirus and Varicella Zoster Virus
De Castro, Sonia
Garcia-Aparicio, Carlos
Andrei, Graciela
Snoeck, Robert
Balzarini, Jan
Camarasa, Maria-Jose
Velazquez, Sonsoles
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (06) : 1582 - 1591
[6] Updating the CSIC Reaction (2003-2020)
Dobrydnev, Alexey V.
Marco-Contelles, Jose
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (08) : 1229 - 1248
[7] Continued Structural Exploration of Sulfocoumarin as Selective Inhibitor of Tumor-Associated Human Carbonic Anhydrases IX and XII
Giovannuzzi, Simone
Capasso, Clemente
Nocentini, Alessio
Supuran, Claudiu T.
[J]. MOLECULES, 2022, 27 (13):
[8] 6-Substituted Sulfocoumarins Are Selective Carbonic Anhdydrase IX and XII Inhibitors with Significant Cytotoxicity against Colorectal Cancer Cells
Grandane, Aiga
Tanc, Muhammet
Mannelli, Lorenzo Di Cesare
Carta, Fabrizio
Ghelardini, Carla
Zalubovskis, Raivis
Supuran, Claudiu T.
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (09) : 3975 - 3983
[9] Synthesis of 6-aryl-substituted sulfocoumarins and investigation of their carbonic anhydrase inhibitory action
Grandane, Aiga
Tanc, Muhammet
Zalubovskis, Raivis
Supuran, Claudiu T.
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2015, 23 (07) : 1430 - 1436
[10] Scalable and sustainable electrochemical allylic C-H oxidation
Horn, Evan J.
Rosen, Brandon R.
Chen, Yong
Tang, Jiaze
Chen, Ke
Eastgate, Martin D.
Baran, Phil S.
[J]. NATURE, 2016, 533 (7601) : 77 - 81

← 1 2 3 4 5 6 →