- Photoredox Catalyzed Sulfonylation of Multisubstituted Allenes with Ru(bpy)3Cl2 or Rhodamine B
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A highly regio- and stereoselective sulfonylation of allenes was developed that provided direct access to α, β-substituted unsaturated sulfone. By means of visible-light photoredox catalysis, the free radicals produced by p-toluenesulfonic acid reacted with multisubstituted allenes to obtain Markovnikov-type vinyl sulfones with Ru(bpy)3Cl2 or Rhodamine B as photocatalyst. The yield of this reaction could reach up to 91%. A series of unsaturated sulfones would be used for further transformation to some valuable compounds.
- Chen, Jingyun,Chen, Shufang,Jiang, Jun,Lu, Qianqian,Shi, Liyang,Xu, Zekun,Yimei, Zhao
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supporting information
(2021/11/09)
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- tert-Butyl Hydroperoxide-Initiated Radical Cyclization of 1-(Allyloxy)-2-(1-Arylvinyl)Benzenes with Sulfinic Acids to Access Sulfonated Benzoxepines
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A tert-butyl hydroperoxide-initiated radical cyclization of 1-(allyloxy)-2-(1-arylvinyl)benzenes with sulfinic acids for the construction of sulfonated benzoxepines is developed. This reaction involves a radical pathway and offers a straightforward route to the formation of seven-membered ring via sulfonylation/cyclization process. This methodology features mild reaction conditions, a broad substrate scope and good functional group tolerance. (Figure presented.).
- Kuang, Kaimo,Wu, Meixia,Wu, Sixin,Xia, Ziqin,Xu, Qiankun,Zhang, Man,Zhou, Nengneng
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supporting information
p. 3491 - 3495
(2021/06/28)
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- Hydrosulfonylation of Alkenes with Sulfonyl Chlorides under Visible Light Activation
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Sulfonyl chlorides are inexpensive reactants extensively explored for functionalization, but never considered for radical hydrosulfonylation of alkenes. Herein, we report that tris(trimethylsilyl)silane is an ideal hydrogen atom donor enabling highly effective photoredox-catalyzed hydrosulfonylation of electron-deficient alkenes with sulfonyl chlorides. To increase the generality of this transformation, polarity-reversal catalysis (PRC) was successfully implemented for alkenes bearing alkyl substituents. This late-stage functionalization method tolerates a remarkably wide range of functional groups, is operationally simple, scalable, and allows access to building blocks which are important for medicinal chemistry and drug discovery.
- Christensen, Kirsten E.,Gouverneur, Véronique,Hell, Sandrine M.,Meyer, Claudio F.,Misale, Antonio,Sap, Jeroen B. I.,Trabanco, Andrés A.,Willis, Michael C.
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supporting information
p. 11620 - 11626
(2020/05/25)
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- Visible-Light-Induced Radical Cascade Cyclizations of 1,7-Enynes with Sulfinic Acids: Direct Access to Sulfonated Chromanes and Sulfonated Tetrahydroquinolines under Metal-Free Conditions
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Visible-light-induced strategy to access sulfonated chromanes and sulfonated 1,2,3,4-tetrahydroquinolines via a radical cascade cyclization of 1-(arylethynyl)-2-(vinyloxy)benzenes and N-allyl-2-(arylethynyl)anilines with aromatic and aliphatic sulfinic acids has been developed. In the presence of TBHP (7.5 mol%) as an oxidant and Eosin Y (3.0 mol%) as a photocatalyst, the reactions undergo smoothly to afford the corresponding products in good yields at room temperature under metal-free conditions. This transformation features low loading of TBHP, mild reaction conditions, simple operation, broad functional-group tolerance, and good yields of products. (Figure presented.).
- Liu, Qi,Mei, Yousheng,Wang, Lei,Ma, Yongmin,Li, Pinhua
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supporting information
p. 5669 - 5680
(2020/10/28)
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- Direct Substitution of Secondary and Tertiary Alcohols to Generate Sulfones under Catalyst- and Additive-Free Conditions
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An environmentally benign protocol that affords propargylic sulfones containing highly congested carbon centers from easily accessible alcohols and sulfinic acids with water as the only byproduct is reported. The reaction proceeded via an in situ dehydrative cross-coupling process by taking advantage of the synergetic actions of multiple hydrogen bonds rather than relying on an external catalyst and/or additives to achieve high product distribution.
- Liu, Yanan,Xie, Peizhong,Sun, Zuolian,Wo, Xiangyang,Gao, Cuiqing,Fu, Weishan,Loh, Teck-Peng
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supporting information
p. 5353 - 5356
(2018/09/13)
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- Synthesis of Substituted Pyrroles via Copper-Catalyzed Cyclization of Ethyl Allenoates with Activated Isocyanides
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A new method for the synthesis of di- and trisubstituted pyrroles via copper-catalyzed cyclization of ethyl allenoates with activated isocyanides has been developed. In contrast to related annulation reactions previously reported, this new process features a skeletal rearrangement in which the aryl sulfonyl moiety, which functions as the electron-withdrawing group in the α-carbon of the isocyanide, was found to migrate to the γ-carbon of the starting allenoate in the final product for the first time.
- Lu, Kui,Ding, Fang,Qin, Long,Jia, Xiaoliang,Xu, Chuanming,Zhao, Xia,Yao, Qingwei,Yu, Peng
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supporting information
p. 2121 - 2125
(2016/08/12)
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- Microwave-accelerated Pd-catalyzed desulfitative direct C2-arylation of free (NH)-indoles with arylsulfinic acids
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The rapid and efficient direct C2-arylation of free (NH)-indoles with arylsulfinic acids proceeded through a microwave-accelerated palladium-catalyzed desulfitation reaction. By using PdCl2 as a catalyst, silver acetate as an oxidant, and H2SO4 as an additive, arylsulfinic acids with both electron-donating and electron-withdrawing groups underwent desulfitative coupling with an array of free (NH)-indoles, thereby selectively providing C2-arylindoles in good yields. From C2 shining sea: The direct C2-arylation of free (NH)-indoles with arylsulfinic acids proceeded through a Pd-catalyzed desulfitation reaction. In the presence of an oxidant and an additive, 2-arylindoles were selectively afforded in good yields. Copyright
- Miao, Tao,Li, Pinhua,Wang, Guan-Wu,Wang, Lei
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p. 3185 - 3190
(2014/01/06)
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- Palladium-catalyzed desulfitative heck-type reaction of aryl sulfinic acids with alkenes
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An efficient protocol has been developed for the desulfitative Heck-type reaction of aryl sulfinic acids with a variety of alkenes in the presence of a catalytic amount of Pd(OAc)2 and inexpensive Cu(OAc)2 as oxidant. This method does not require a ligand or a base, thereby broadening the scope of Pd-catalyzed coupling reactions. Copyright
- Wang, Guan-Wu,Miao, Tao
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supporting information; experimental part
p. 5787 - 5790
(2011/06/23)
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- Synthesis of ketones by palladium-catalysed desulfitative reaction of arylsulfinic acids with nitriles
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Palladium-catalysed desulfitative addition of arylsulfinic acids to aryl and alkyl nitriles with 2,2′-bipyridine as a ligand afforded a variety of aryl ketones via hydrolysis of ketimine intermediates.
- Miao, Tao,Wang, Guan-Wu
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supporting information; experimental part
p. 9501 - 9503
(2011/10/01)
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- Amide analogs of antifungal dioxane-triazole derivatives: Synthesis and in vitro activities
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A new series of triazole compounds possessing an amide-part were efficiently synthesized and their in vitro antifungal activities were investigated. The amide analogs showed excellent in vitro activity against Candida, Cryptococcus and Aspergillus species
- Uchida, Takuya,Kagoshima, Yoshiko,Konosu, Toshiyuki
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scheme or table
p. 2013 - 2017
(2009/11/30)
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- Thyromimetic organic compounds
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Compounds of the present invention of the formula are thyromimetic agents which can be used to prevent and/or treat diseases associated with an imbalance of thyroid hormones, such as hypo- and hyper-thyroidism, obesity, osteoporosis and depression. The co
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- Discovery of Small-Molecule Inhibitors of the ATPase Activity of Human Papillomavirus E1 Helicase
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The Boehringer Ingelheim compound collection was screened for inhibitors of the ATPase activity of human papillomavirus E1 helicase to develop antiviral agents that inhibit human papillomavirus (HPV) DNA replication. This screen led to the discovery of (biphenyl-4-sulfonyl)acetic acid 1, which inhibits the ATPase activity of HPV type 6 E1 helicase with a low micromolar IC50 value. A hit-to-lead exercise rapidly converted 1 into a low nanomolar lead series.
- Faucher, Anne-Marie,White, Peter W.,Brochu, Christian,Grand-Ma?tre, Chantal,Rancourt, Jean,Fazal, Gulrez
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- Indole carboxylic acids as thyroid receptor ligands
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A compound of the formula wherein W, R1, R2, R3, R4, R5, R6, R7, R8 and R13 are as defined herein, useful in the treatment of obesity, overweight condition, hyperlipidemia, glaucoma, cardiac arrhythmias, skin disorders, thyroid disease, hypothyroidism, th
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- Thyromimetic organic compounds
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Compounds of the present invention of the formula are thyromimetic agents which can be used to prevent and/or treat diseases associated with an imbalance of thyroid hormones, such as hypo- and hyper-thyroidism, obesity, osteoporosis and depression. The co
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- Malonamic acids and derivatives thereof as thyroid receptor ligands
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The present invention relates to novel thyroid receptor ligands and, more particularly, relates to malonamic acids and derivatives thereof of Formula 1, which are useful in the treatment of obesity, overweight condition, hyperlipidemia, glaucoma, cardiac
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- 19F NMR Study of the Reaction of p-Fluorobenzenethiol and Disulfide with Periodate and Other Selected Oxidizing Agents
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The products of the reactions of both p-fluorobenzenethiol and p-fluorobenzene disulfide with a series of oxidants were examined using 19F NMR spectroscopy.Two commonly used mild oxidants (periodate and hydrogen peroxide), a "non-oxygen-transfer" oxidant
- Evans, Brian J.,Doi, Joyce Takahashi,Musker, W. Kenneth
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p. 2337 - 2344
(2007/10/02)
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