The Experts below are selected from a list of 228 Experts worldwide ranked by ideXlab platform
Modhu Sudan Maji - One of the best experts on this subject based on the ideXlab platform.
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Transition-Metal-Free Redox-Neutral One-Pot C3-Alkenylation of Indoles Using Aldehydes
Organic letters, 2017Co-Authors: Samrat Sahu, Ankush Banerjee, Modhu Sudan MajiAbstract:The synthesis of sensitive β-alkyl 3-vinylindoles having diverse functional groups with good selectivity remains a challenging task. Keeping the synthetic utility of 3-alkenylindoles in mind, we explored a unique approach to synthesize them from unprotected indoles in a domino fashion. A transition-metal-free C3-alkenylation of indole is reported by using sequential Bronsted Acid/base catalysis. Several β-substituted 3-alkenylindoles and conjugated 1,3-dienes are synthesized by direct coupling of indole and readily available aliphatic aldehydes. Excellent scalability and recycling of Benzenesulfinic Acid for successive alkenylation reactions up to five times make this method economically viable.
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Transition-Metal-Free Redox-Neutral One-Pot C3-Alkenylation of Indoles Using Aldehydes
2017Co-Authors: Samrat Sahu, Ankush Banerjee, Modhu Sudan MajiAbstract:The synthesis of sensitive β-alkyl 3-vinylindoles having diverse functional groups with good selectivity remains a challenging task. Keeping the synthetic utility of 3-alkenylindoles in mind, we explored a unique approach to synthesize them from unprotected indoles in a domino fashion. A transition-metal-free C3-alkenylation of indole is reported by using sequential Brønsted Acid/base catalysis. Several β-substituted 3-alkenylindoles and conjugated 1,3-dienes are synthesized by direct coupling of indole and readily available aliphatic aldehydes. Excellent scalability and recycling of Benzenesulfinic Acid for successive alkenylation reactions up to five times make this method economically viable
Samrat Sahu - One of the best experts on this subject based on the ideXlab platform.
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Transition-Metal-Free Redox-Neutral One-Pot C3-Alkenylation of Indoles Using Aldehydes
Organic letters, 2017Co-Authors: Samrat Sahu, Ankush Banerjee, Modhu Sudan MajiAbstract:The synthesis of sensitive β-alkyl 3-vinylindoles having diverse functional groups with good selectivity remains a challenging task. Keeping the synthetic utility of 3-alkenylindoles in mind, we explored a unique approach to synthesize them from unprotected indoles in a domino fashion. A transition-metal-free C3-alkenylation of indole is reported by using sequential Bronsted Acid/base catalysis. Several β-substituted 3-alkenylindoles and conjugated 1,3-dienes are synthesized by direct coupling of indole and readily available aliphatic aldehydes. Excellent scalability and recycling of Benzenesulfinic Acid for successive alkenylation reactions up to five times make this method economically viable.
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Transition-Metal-Free Redox-Neutral One-Pot C3-Alkenylation of Indoles Using Aldehydes
2017Co-Authors: Samrat Sahu, Ankush Banerjee, Modhu Sudan MajiAbstract:The synthesis of sensitive β-alkyl 3-vinylindoles having diverse functional groups with good selectivity remains a challenging task. Keeping the synthetic utility of 3-alkenylindoles in mind, we explored a unique approach to synthesize them from unprotected indoles in a domino fashion. A transition-metal-free C3-alkenylation of indole is reported by using sequential Brønsted Acid/base catalysis. Several β-substituted 3-alkenylindoles and conjugated 1,3-dienes are synthesized by direct coupling of indole and readily available aliphatic aldehydes. Excellent scalability and recycling of Benzenesulfinic Acid for successive alkenylation reactions up to five times make this method economically viable
V. V. Razin - One of the best experts on this subject based on the ideXlab platform.
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Synthesis of Tricyclo[4.4.0.02,7]decane Derivatives from Tricyclo[4.1.0.02,7]heptane Precursors
Russian Journal of Organic Chemistry, 2019Co-Authors: V. A. Vasin, V. V. Razin, D. Yu. Korovin, P. S. PetrovAbstract:Tricyclo[4.1.0.02,7]heptane and 1-phenyltricyclo[4.1.0.02,7]heptane reacted with 2,3-bis(benzenesulfonyl)propene in boiling toluene (20–24 h) in the presence of benzoyl peroxide via trans-selective cleavage of the C1–C7 central bicyclobutane bond to give 6(7)-syn-benzenesulfonyl-7(6)-exo-[2-(benzenesulfonyl)prop-2-en-1-yl]bicyclo[3.1.1]heptane derivatives. The latter underwent cyclization to 1,9- and 7,9-bis(benzenesulfonyl)tricyclo[4.4.0.02,7]decane derivatives by the action of potassium tert-butoxide in dioxane at 50°C as a result of intramolecular Michael addition. Heating of the cyclization products in dioxane at 100°C in the presence of potassium tert-butoxide resulted in elimination of Benzenesulfinic Acid molecule with the formation of mixtures of two isomeric benzenesulfonyl-substituted tricyclo[4.4.0.02,7]dec-3-enes.
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Synthesis of Tricyclo[4.4.0.0^2,7]decane Derivatives from Tricyclo[4.1.0.0^2,7]heptane Precursors
Russian Journal of Organic Chemistry, 2019Co-Authors: V. A. Vasin, V. V. Razin, D. Yu. Korovin, P. S. PetrovAbstract:Tricyclo[4.1.0.0^2,7]heptane and 1-phenyltricyclo[4.1.0.0^2,7]heptane reacted with 2,3-bis(benzenesulfonyl)propene in boiling toluene (20–24 h) in the presence of benzoyl peroxide via trans -selective cleavage of the C^1–C^7 central bicyclobutane bond to give 6(7)- syn -benzenesulfonyl-7(6)- exo -[2-(benzenesulfonyl)prop-2-en-1-yl]bicyclo[3.1.1]heptane derivatives. The latter underwent cyclization to 1,9- and 7,9-bis(benzenesulfonyl)tricyclo[4.4.0.0^2,7]decane derivatives by the action of potassium tert -butoxide in dioxane at 50°C as a result of intramolecular Michael addition. Heating of the cyclization products in dioxane at 100°C in the presence of potassium tert -butoxide resulted in elimination of Benzenesulfinic Acid molecule with the formation of mixtures of two isomeric benzenesulfonyl-substituted tricyclo[4.4.0.0^2,7]dec-3-enes.
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First synthesis of nitro-substituted bicyclo[1.1.0]butane derivatives and new method for generation of tricyclo[4.1.0.0^2,7]hept-1(7)-ene
Russian Journal of Organic Chemistry, 2007Co-Authors: V. A. Vasin, S. G. Kostryukov, R. N. Zolotarev, V. V. RazinAbstract:Successive treatment of 1-phenylsulfonyltricyclo[4.1.0.0^2,7]heptane with butyllithium and ethyl nitrate leads to the formation of 7-nitro-7′-phenylsulfonyl-1,1′-bi(tricyclo[4.1.0.0^2,7]heptane) through intermediate tricyclo[4.1.0.0^2,7]hept-1(7)-ene which is generated by 1,2-elimination of Benzenesulfinic Acid from the initial compound. Analogous treatment of 1-phenyltricyclo[4.1.0.0^2,7]heptane gives 1-nitro-7-phenyltricyclo[4.1.0.0^2,7]heptane.
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First synthesis of nitro-substituted bicyclo[1.1.0]butane derivatives and new method for generation of tricyclo[4.1.0.02,7]hept-1(7)-ene
Russian Journal of Organic Chemistry, 2007Co-Authors: V. A. Vasin, S. G. Kostryukov, R. N. Zolotarev, V. V. RazinAbstract:Successive treatment of 1-phenylsulfonyltricyclo[4.1.0.02,7]heptane with butyllithium and ethyl nitrate leads to the formation of 7-nitro-7′-phenylsulfonyl-1,1′-bi(tricyclo[4.1.0.02,7]heptane) through intermediate tricyclo[4.1.0.02,7]hept-1(7)-ene which is generated by 1,2-elimination of Benzenesulfinic Acid from the initial compound. Analogous treatment of 1-phenyltricyclo[4.1.0.02,7]heptane gives 1-nitro-7-phenyltricyclo[4.1.0.02,7]heptane.
V. A. Vasin - One of the best experts on this subject based on the ideXlab platform.
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Synthesis of Tricyclo[4.4.0.02,7]decane Derivatives from Tricyclo[4.1.0.02,7]heptane Precursors
Russian Journal of Organic Chemistry, 2019Co-Authors: V. A. Vasin, V. V. Razin, D. Yu. Korovin, P. S. PetrovAbstract:Tricyclo[4.1.0.02,7]heptane and 1-phenyltricyclo[4.1.0.02,7]heptane reacted with 2,3-bis(benzenesulfonyl)propene in boiling toluene (20–24 h) in the presence of benzoyl peroxide via trans-selective cleavage of the C1–C7 central bicyclobutane bond to give 6(7)-syn-benzenesulfonyl-7(6)-exo-[2-(benzenesulfonyl)prop-2-en-1-yl]bicyclo[3.1.1]heptane derivatives. The latter underwent cyclization to 1,9- and 7,9-bis(benzenesulfonyl)tricyclo[4.4.0.02,7]decane derivatives by the action of potassium tert-butoxide in dioxane at 50°C as a result of intramolecular Michael addition. Heating of the cyclization products in dioxane at 100°C in the presence of potassium tert-butoxide resulted in elimination of Benzenesulfinic Acid molecule with the formation of mixtures of two isomeric benzenesulfonyl-substituted tricyclo[4.4.0.02,7]dec-3-enes.
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Synthesis of Tricyclo[4.4.0.0^2,7]decane Derivatives from Tricyclo[4.1.0.0^2,7]heptane Precursors
Russian Journal of Organic Chemistry, 2019Co-Authors: V. A. Vasin, V. V. Razin, D. Yu. Korovin, P. S. PetrovAbstract:Tricyclo[4.1.0.0^2,7]heptane and 1-phenyltricyclo[4.1.0.0^2,7]heptane reacted with 2,3-bis(benzenesulfonyl)propene in boiling toluene (20–24 h) in the presence of benzoyl peroxide via trans -selective cleavage of the C^1–C^7 central bicyclobutane bond to give 6(7)- syn -benzenesulfonyl-7(6)- exo -[2-(benzenesulfonyl)prop-2-en-1-yl]bicyclo[3.1.1]heptane derivatives. The latter underwent cyclization to 1,9- and 7,9-bis(benzenesulfonyl)tricyclo[4.4.0.0^2,7]decane derivatives by the action of potassium tert -butoxide in dioxane at 50°C as a result of intramolecular Michael addition. Heating of the cyclization products in dioxane at 100°C in the presence of potassium tert -butoxide resulted in elimination of Benzenesulfinic Acid molecule with the formation of mixtures of two isomeric benzenesulfonyl-substituted tricyclo[4.4.0.0^2,7]dec-3-enes.
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First synthesis of nitro-substituted bicyclo[1.1.0]butane derivatives and new method for generation of tricyclo[4.1.0.0^2,7]hept-1(7)-ene
Russian Journal of Organic Chemistry, 2007Co-Authors: V. A. Vasin, S. G. Kostryukov, R. N. Zolotarev, V. V. RazinAbstract:Successive treatment of 1-phenylsulfonyltricyclo[4.1.0.0^2,7]heptane with butyllithium and ethyl nitrate leads to the formation of 7-nitro-7′-phenylsulfonyl-1,1′-bi(tricyclo[4.1.0.0^2,7]heptane) through intermediate tricyclo[4.1.0.0^2,7]hept-1(7)-ene which is generated by 1,2-elimination of Benzenesulfinic Acid from the initial compound. Analogous treatment of 1-phenyltricyclo[4.1.0.0^2,7]heptane gives 1-nitro-7-phenyltricyclo[4.1.0.0^2,7]heptane.
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First synthesis of nitro-substituted bicyclo[1.1.0]butane derivatives and new method for generation of tricyclo[4.1.0.02,7]hept-1(7)-ene
Russian Journal of Organic Chemistry, 2007Co-Authors: V. A. Vasin, S. G. Kostryukov, R. N. Zolotarev, V. V. RazinAbstract:Successive treatment of 1-phenylsulfonyltricyclo[4.1.0.02,7]heptane with butyllithium and ethyl nitrate leads to the formation of 7-nitro-7′-phenylsulfonyl-1,1′-bi(tricyclo[4.1.0.02,7]heptane) through intermediate tricyclo[4.1.0.02,7]hept-1(7)-ene which is generated by 1,2-elimination of Benzenesulfinic Acid from the initial compound. Analogous treatment of 1-phenyltricyclo[4.1.0.02,7]heptane gives 1-nitro-7-phenyltricyclo[4.1.0.02,7]heptane.
Mark J. Coster - One of the best experts on this subject based on the ideXlab platform.
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Arylation of [6,6]-Spiroacetal Enol Ethers: Reactivity and Rearrangement.
ChemInform, 2011Co-Authors: Kylee Maree Aumann, Peter Conrad Healy, Mark J. CosterAbstract:The Pd-catalyzed arylation of methyl derivative (I) gives the double-Heck product (III), whereas reaction with Benzenesulfinic Acid (IV) results in rearrangement to produce chroman structures (V) and (XI).
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Arylation of [6,6]-spiroacetal enol ethers: reactivity and rearrangement
Tetrahedron Letters, 2011Co-Authors: Kylee Maree Aumann, Peter Conrad Healy, Mark J. CosterAbstract:Attempts to selectively arylate [6,6]-spiroacetal enol ethers at the 2-position delivered unexpected results. Palladium-mediated arylation conditions afforded the double-Heck product, whereas reaction with Benzenesulfinic Acid resulted in a facile rearrangement into the corresponding 5-phenylsulfonyl-3,4,5,6-tetrahydrochromans, providing access to 5-aryl-3,4,5,6-tetrahydrochroman and hexahydrochroman derivatives.