- Organophotoredox-Catalyzed Formation of Alkyl-Aryl and -Alkyl C-S/Se Bonds from Coupling of Redox-Active Esters with Thio/Selenosulfonates
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A mild organophotoredox synthetic protocol for forming a Csp3-S/Se bond by reacting widespread redox-active esters with thio/selenosulfonates has been developed. The power of the synthetic manifold is fueled by an unprecedented broad substrate scope and wide functional group tolerance.
- Dong, Yue,Ji, Peng,Zhang, Yueteng,Wang, Changqing,Meng, Xiang,Wang, Wei
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p. 9562 - 9567
(2021/01/09)
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- Triflic acid catalyzed reductive coupling reactions of carbonyl compounds with O-, S-, and N-nucleophiles
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Highly efficient metal-free reductive coupling reactions of aldehydes and ketones with a range of nucleophiles in the presence of triflic acid (1-5 mol %) as the catalyst are presented. The reactions can be performed at ambient temperature without exclusion of moisture or air. A range of symmetrical and unsymmetrical ethers were obtained by this method in high yields and short reaction times. For the first time, the influence of additional functionalization has been studied. Furthermore, the formation of thioethers from ketones (by addition of unmodified thiols) and of sulfonamides from either aldehydes or ketones has been achieved under catalytic conditions.
- Gellert, Beate A.,Kahlcke, Nils,Feurer, Markus,Roth, Stefanie
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supporting information; experimental part
p. 12203 - 12209
(2011/11/07)
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- Boron trifluoride monohydrate catalyzed one-flask preparation of sulfides from carbonyl compounds with thiols and triethylsilane
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Boron trifluoride monohydrate catalyzed thiolation of aldehydes and ketones with thiols and triethylsilane to the corresponding sulfides was carried out in good to excellent yields.
- Olah,Wang,Trivedi,Prakash
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p. 465 - 4466
(2007/10/02)
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- TETRAPHOSPHORUS TRISULFIDE IN REACTIONS WITH THIOACETALS, AMINALS, SULFENAMIDES AND DISULFIDES. INFLUENCE OF AMINES AND BENZOYL PEROXIDE
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The reactions of tetraphosphorus trisulfide with thioacetals, aminals, sulfenamides and disulfides were studied.The reactions were found to give organothiophosphorus compounds and to be facilitated by organic amines and benzoyl peroxide.Key words: Tetraphosphorus trisulfide; thioacetals; aminals; sulfenamides; disulfides; organothiophosphorus compounds.
- Nizamov, Il'yas S.,Batyeva, Elvira S.,Al'fonsov, Vladimir A.,Musin, Rashid Z.,Pudovik, Arkady N.
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p. 229 - 237
(2007/10/02)
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- A Novel Catalyst System, Trimethylsilyl Chloride and Indium(III) Chloride, as an Efficient Catalyst in the Sulfide Synthesis
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O-Trimethylsilyl monothioacetals, which are generally difficult to activate under acidic conditions due to their rapid disproportionation, smoothly react with triethylsilane in the presence of a novel catalyst system, trimethylsilyl chloride and indium(III) chloride, to afford the corresponding sulfides in good to high yields.One pot synthesis of sulfides from aldehydes is also attained in high yields by successive treatment of aldehydes with trimethylsilyl alkyl (aryl) sulfides and triethylsilane in the presence of the above catalyst system under extremely mild conditions.
- Mukaiyama, Teruaki,Ohno, Takashi,Nishimura, Takashi,Han, Jeong Sik,Kobayashi, Shu
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p. 2524 - 2527
(2007/10/02)
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- An Effective Activation of O-Trimethylsilyl Monothioacetal under Extremely Mild Conditions Using a Novel Catalyst System, Trimethylsilyl Chloride and Indium(III) Chloride
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A novel catalyst system, trimethylsilyl chloride and indium(III) chloride, effectively catalyzes the reaction of O-trimethylsilyl monothioacetals with triethylsilane and silylated carbon nucleophiles, respectively, to afford the corresponding sulfide derivatives in good to high yields.
- Mukaiyama, Teruaki,Ohno, Takashi,Nishimura, Takashi,Han, Jeong Sik,Kobayashi, Shu
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p. 2239 - 2242
(2007/10/02)
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- MODERN FRIEDEL-CRAFTS CHEMISTRY. XI. CYCLIZATION OF ARYL HALOALKYL SULFONES, ARYLSULFONYLACYL CHLORIDES AND THEIR CORRESPONDING SULFIDES
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The sulfone group deactivation for cyclialkylation and cycliacylation reactions in the presence of Friedel-Crafts catalysts was demonstrated in a number of aryl chloroalkylsulfones (1-8) and arylsulfonylacyl chlorides (17a-22a), respectively.As expected, the corresponding arylchloroalkyl sulfides (9-16) and arylmercaptoacyl chlorides (13a-28a) underwent ring-closure reaction in most cases under the same conditions.The ease of cyclization was governed by the ring size, the stability of the attacking carbocation and the nucleophilicity of the aryl moiety.Also, the behaviour of benzyl sulfones (29, 31a, and 32a) and sulfides (33, 34a and 36a) was inconsistent.Noteworthy, the Friedel-Crafts cyclization reaction is thus considered an accessible method for the synthesis of compounds 37-41 and 45, 51.
- Abdel-Wahab, Aboel-Magd A.,El-Khawaga, Ahmed M.,El-Zohry, Maher F.,Khalaf, Ali A.
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- An Odorless Preparative Method of Sulfides and Thiocarboxylic S-Esters Using 3-(Alkylthio)-1,2-benzisothiazole 1,1-Dioxide
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It was found that sodium salt of 1,2-benzisothiazole-3(2H)-thione 1,1-dioxide (thiosaccharin) readily reacted with alkyl halide affording 3-(alkylthio)-1,2-benzisothiazole 1,1-dioxide (3).Treatment of 3 with piperidine produces the corresponding alkanethiol in situ quantitatively and subsequent treatment with various electrophiles gives the corresponding sulfides and thiocarboxylic S-esters in good yields.
- Yamada, Hiroyuki,Kinoshita, Hideki,Inomata, Katsuhiko,Kotake, Hiroshi
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p. 949 - 950
(2007/10/02)
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- Novel Synthetic Reactions Using Bis(2,2,2-trifluoroethoxy)triphenylphosphorane
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Alkoxy-or (acyloxy)(2,2,2-trifluoroethoxy)triphenylphosphoranes which were prepared in situ by the ligand exchange of bis(2,2,2-trifluoroethoxy)triphenylphosphorane with alcohols or carboxylic acids were found to behave as potential alkylating or acylating reagents for the preparation of a variety of esters, amides, sulfides, and ketones.
- Kubota, Toshio,Miyashita, Satoshi,Kitazume, Tomoya,Ishikawa, Nobuo
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p. 5052 - 5057
(2007/10/02)
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