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References (48)
-
Darryl Boyd (2016)
Schwefel in der modernen MaterialwissenschaftAngewandte Chemie, 128
-
M. Iwasaki, Miki Iyanaga, Yuta Tsuchiya, Y. Nishimura, Wenjuan Li, Zhiping Li, Y. Nishihara (2014)
Palladium-catalyzed direct thiolation of aryl C-H bonds with disulfides.Chemistry, 20 9
-
D. Liaw, Been-Yang Liaw (1999)
Synthesis and properties of new polyimides derived from 1,1-bis[4-(4-aminophenoxy)phenyl]cyclododecanePolymer, 40
-
Shouhui Zhang, Pengcheng Qian, Manli Zhang, Mao‐Lin Hu, Jiang Cheng (2010)
Copper-catalyzed thiolation of the di- or trimethoxybenzene arene C-H bond with disulfides.The Journal of organic chemistry, 75 19
-
Jhih-Ru Wu, Che‐Hung Lin, Chin‐Fa Lee (2009)
Iron-catalyzed thioetherification of thiols with aryl iodides.Chemical communications, 29
-
J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire (2002)
Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.Chemical reviews, 102 5
-
H. Firouzabadi*, N. Iranpoor*, M. Gholinejad (2010)
One-Pot Thioetherification of Aryl Halides Using Thiourea and Alkyl Bromides Catalyzed by Copper(I) Iodide Free from Foul-Smelling Thiols in Wet Polyethylene Glycol (PEG 200)Advanced Synthesis & Catalysis, 352
-
P. Gehrtz, V. Geiger, Tanno Schmidt, L. Sršan, I. Fleischer (2018)
Cross-Coupling of Chloro(hetero)arenes with Thiolates Employing a Ni(0)-Precatalyst.Organic letters, 21 1
-
C. Galli, T. Pau (1998)
The dehalogenation reaction of organic halides by tributyltin radical: The energy of activation vs. the BDE of the CX bondTetrahedron, 54
-
M. Feng, Bingqing Tang, Steven Liang, Xuefeng Jiang (2016)
Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry.Current topics in medicinal chemistry, 16 11
-
T. Scattolin, E. Senol, Guoyin Yin, Q. Guo, Franziska Schoenebeck (2018)
Site‐Selective C−S Bond Formation at C−Br over C−OTf and C−Cl Enabled by an Air‐Stable, Easily Recoverable, and Recyclable Palladium(I) CatalystAngewandte Chemie (International Ed. in English), 57
-
Shou-Ri Sheng, Wei Zhang, Chunwei Lu, Jiong Wan, Xiao-Ling Liu, Cai-sheng Song (2012)
Synthesis and characterization of new cardo poly(ether imide)s derived from 9,9‐bis [4‐(4‐aminophenoxy)phenyl]xantheneJournal of Applied Polymer Science, 126
-
Fang Ke, Yanyang Qu, Zhaoqiong Jiang, Zhengkai Li, Di Wu, Xiangge Zhou (2011)
An efficient copper-catalyzed carbon-sulfur bond formation protocol in water.Organic letters, 13 3
-
A. Gangjee, Yibin Zeng, Tina Talreja, J. McGuire, R. Kisliuk, S. Queener (2007)
Design and synthesis of classical and nonclassical 6-arylthio-2,4-diamino-5-ethylpyrrolo[2,3-d]pyrimidines as antifolates.Journal of medicinal chemistry, 50 13
-
V. Reddy, K. Swapna, A. Kumar, K. Rao (2009)
Indium-catalyzed C-S cross-coupling of aryl halides with thiols.The Journal of organic chemistry, 74 8
-
Rina Sikari, S. Sinha, Siuli Das, Anannya Saha, G. Chakraborty, R. Mondal, N. Paul (2019)
Achieving Nickel Catalyzed C-S Cross-Coupling under Mild Conditions Using Metal-Ligand Cooperativity.The Journal of organic chemistry, 84 7
-
M. Kosugi,, T. Shimizu, T. Migita (1978)
Reactions of aryl halides with thiolate anions in the presence of catalytic amounts of tetrakis(triphenylphosphine)palladium. Preparation of aryl sulfides.Chemistry Letters, 7
-
Miki Murata, S. Buchwald (2004)
A general and efficient method for the palladium-catalyzed cross-coupling of thiols and secondary phosphinesTetrahedron, 60
-
N. Taniguchi (2004)
Alkyl- or arylthiolation of aryl iodide via cleavage of the S-S bond of disulfide compound by nickel catalyst and zinc.The Journal of organic chemistry, 69 20
-
P. Koning, L. Murtagh, J. Lawson, R. Embse, S. Kunda, W. Kong (2011)
Development an Efficient Route to the 5-Lipoxygenase Inhibitor PF-04191834Organic Process Research & Development, 15
-
T. Migita, T. Shimizu, Y. Asami, Jun-ichi Shiobara, Yasuki Kato, M. Kosugi, (1980)
The Palladium Catalyzed Nucleophilic Substitution of Aryl Halides by Thiolate AnionsBulletin of the Chemical Society of Japan, 53
-
S. Buchwald, Carsten Bolm (2012)
On the Role of Metal Contaminants in Catalyses with FeCl -
Yugen Zhang, K. Ngeow, J. Ying (2007)
The first N-heterocyclic carbene-based nickel catalyst for C-S coupling.Organic letters, 9 18
-
Kieran Jones, Dennis Power, D. Bierer, K. Gericke, S. Stewart (2018)
Nickel Phosphite/Phosphine-Catalyzed C-S Cross-Coupling of Aryl Chlorides and Thiols.Organic letters, 20 1
-
Krista Wager, Matthew Daniels (2011)
Palladium-catalyzed cross-coupling of benzyl thioacetates and aryl halides.Organic letters, 13 15
-
G. Martino, Michael Edler, G. Regina, Antonio Coluccia, M. Barbera, D. Barrow, R. Nicholson, G. Chiosis, A. Brancale, E. Hamel, M. Artico, R. Silvestri (2006)
New arylthioindoles: potent inhibitors of tubulin polymerization. 2. Structure-activity relationships and molecular modeling studies.Journal of medicinal chemistry, 49 3
-
A. Correa, M. Carril, C. Bolm (2008)
Iron-catalyzed S-arylation of thiols with aryl iodides.Angewandte Chemie, 47 15
-
I. Beletskaya, V. Ananikov (2011)
Transition-metal-catalyzed C-S, C-Se, and C-Te bond formation via cross-coupling and atom-economic addition reactions.Chemical reviews, 111 3
-
F. Bickelhaupt, K. Houk (2017)
Das Distortion/Interaction‐Activation‐Strain‐Modell zur Analyse von ReaktionsgeschwindigkeitenAngewandte Chemie, 129
-
J. Hartwig (2008)
Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides.Accounts of chemical research, 41 11
-
C. Eichman, J. Stambuli (2011)
Transition Metal Catalyzed Synthesis of Aryl SulfidesMolecules, 16
-
Valentin Magné, Liam Ball (2019)
Synthesis of Air-stable, Odorless Thiophenol Surrogates via Ni-Catalyzed C-S Cross-Coupling.Chemistry
-
V. Reddy, Akkilagunta Kumar, K. Swapna, K. Rao (2009)
Nano indium oxide as a recyclable catalyst for C-S cross-coupling of thiols with aryl halides under ligand free conditions.Organic letters, 11 8
-
M. Fernández-Rodríguez, J. Hartwig (2009)
A general, efficient, and functional-group-tolerant catalyst system for the palladium-catalyzed thioetherification of aryl bromides and iodides.The Journal of organic chemistry, 74 4
-
A. Meijere, F. Diederich (2004)
Metal-catalyzed cross-coupling reactions -
C. Palomo, M. Oiarbide, R. López, E. Gómez-Bengoa (2000)
Phosphazene bases for the preparation of biaryl thioethers from aryl iodides and arenethiolsTetrahedron Letters, 41
-
S. Buchwald, C. Bolm (2009)
On the role of metal contaminants in catalyses with FeCl3.Angewandte Chemie, 48 31
-
N. Park, Kyungho Park, Mihee Jang, Sunwoo Lee (2011)
One-pot synthesis of symmetrical and unsymmetrical aryl sulfides by Pd-catalyzed couplings of aryl halides and thioacetates.The Journal of organic chemistry, 76 11
-
D. Boyd (2016)
Sulfur and Its Role In Modern Materials Science.Angewandte Chemie, 55 50
-
Elizabeth Ilardi, Edon Vitaku, J. Njardarson (2014)
Data-mining for sulfur and fluorine: an evaluation of pharmaceuticals to reveal opportunities for drug design and discovery.Journal of medicinal chemistry, 57 7
-
F. Bickelhaupt, K. Houk (2017)
Analyzing Reaction Rates with the Distortion/Interaction‐Activation Strain ModelAngewandte Chemie (International Ed. in English), 56
-
Ying-Chieh Wong, T. Jayanth, Chien‐Hong Cheng (2006)
Cobalt-catalyzed aryl-sulfur bond formation.Organic letters, 8 24
-
E. Álvaro, J. Hartwig (2009)
Resting state and elementary steps of the coupling of aryl halides with thiols catalyzed by alkylbisphosphine complexes of palladium.Journal of the American Chemical Society, 131 22
-
B. Ranu, Amit Saha, R. Jana (2007)
Microwave-assisted simple and efficient ligand free copper nanoparticle catalyzed aryl-sulfur bond formationAdvanced Synthesis & Catalysis, 349
-
D. Prasad, G. Sekar (2011)
Cu-catalyzed one-pot synthesis of unsymmetrical diaryl thioethers by coupling of aryl halides using a thiol precursor.Organic letters, 13 5
-
M. Fernández-Rodríguez, Q. Shen, J. Hartwig (2006)
Highly efficient and functional-group-tolerant catalysts for the palladium-catalyzed coupling of aryl chlorides with thiols.Chemistry, 12 30
-
M. Fernández-Rodríguez, Q. Shen, J. Hartwig (2006)
A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols.Journal of the American Chemical Society, 128 7
-
M. Fernández-Rodríguez, J. Hartwig (2010)
One-pot synthesis of unsymmetrical diaryl thioethers by palladium-catalyzed coupling of two aryl bromides and a thiol surrogate.Chemistry, 16 8
- Publisher
- Wiley
- Copyright
- © 2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
- ISSN
- 2193-5807
- eISSN
- 2193-5815
- DOI
- 10.1002/ajoc.202000025
- Publisher site
- See Article on Publisher Site
Abstract
A simple and effective method for palladium‐catalyzed carbon‐sulfur bond formation was established with aryl thioacetates and chloro(hetero)arenes as starting materials. A wide range of thioacetates and chloro(hetero)arenes can be employed for the preparation of aryl sulfides in good to excellent yield.
Journal
Asian Journal of Organic Chemistry – Wiley
Published: Feb 1, 2020
Keywords: ; ; ; ;