Iodine-Mediated Sulfenylation of Imidazo[1,2-a]pyridines with Ethyl Arylsulfinates

Synlett ◽  
2021 ◽  
Author(s):  
Dong Tang ◽  
Jian Sun ◽  
Yangxiu Mu ◽  
Zafar Iqbal ◽  
Jing Hou ◽  
...  
Keyword(s):  
Reaction Process ◽  
Mild Conditions ◽  
Plausible Mechanism

AbstractA simple iodine-mediated approach is reported for the synthesis of sulfenylated imidazo[1,2-a]pyridines through the reaction of imidazo[1,2-a]pyridines with ethyl arylsulfinates under mild conditions. The reaction scope was investigated, and a plausible mechanism is proposed to elucidate the reaction process and activation mode. The results indicate that ethyl sulfinates are efficient sulfur sources for the construction of C–S bonds.

Fe(NO3)3·9H2O-catalyzed aerobic oxidative deoximation of ketoximes and aldoximes under mild conditions

2018 ◽  
Vol 96 (8) ◽  
pp. 810-814 ◽  
Author(s):  
Yongshu Li ◽  
Nizhou Xu ◽  
Guangyao Mei ◽  
Yun Zhao ◽  
Yiyong Zhao ◽  
...  
Keyword(s):  
Molecular Oxygen ◽  
Functional Groups ◽  
Environmentally Benign ◽  
Synthetic Method ◽  
Simple Process ◽  
Practical Applications ◽  
Mild Conditions ◽  
Excellent Yield ◽  
Wide Range ◽  
Plausible Mechanism

A mild, simple process for the effective aerobic oxidative deoximation of a wide range of ketoximes and aldoximes has been developed that utilizes Fe(NO3)3·9H2O as the single catalyst and molecular oxygen as the green oxidant. The environmentally benign protocol provides moderate to excellent yield and broad functional groups tolerance and is a valuable synthetic method for practical applications. According the relevant verification experiment, a plausible mechanism has been proposed.

Baeyer-Villiger oxidation of ketones catalyzed by iron(III) meso-tetraphenylporphyrin chloride in the presence of molecular oxygen

2008 ◽  
Vol 12 (02) ◽  
pp. 94-100 ◽  
Author(s):  
Xian-Tai Zhou ◽  
Hong-Bing Ji ◽  
Qiu-Lan Yuan
Keyword(s):  
Molecular Oxygen ◽  
Selective Oxidation ◽  
Large Scale ◽  
Turnover Number ◽  
Mild Conditions ◽  
Factors Influencing ◽  
Oxidation By Molecular Oxygen ◽  
Excellent Activity ◽  
Plausible Mechanism ◽  
Villiger Oxidation

Efficient selective oxidation of ketones to lactones by molecular oxygen with benzaldehyde as an oxygen acceptor, in the presence of metalloporphyrins, has been reported. Iron(III) meso-tetraphenylporphyrin chloride ( Fe ( TPP ) Cl ) showed excellent activity and selectivity for oxidation of cyclohexanones under mild conditions. Moreover, different factors influencing ketones oxidation, e.g. catalyst, solvent, temperature and additive, have been investigated. The turnover number (TON) of the Fe ( TPP ) Cl catalyst could reach up to 71000 in a large scale oxidation of cyclohexanone. A plausible mechanism of ketone oxidation by molecular oxygen in the presence of metalloporphyrins and benzaldehyde was proposed.

Hydrazo coupling: the efficient transition-metal-free C–H functionalization of 8-hydroxyquinoline and phenol through base catalysis

2019 ◽  
Vol 21 (23) ◽  
pp. 6381-6389 ◽  
Author(s):  
Pavel N. Solyev ◽  
Daria K. Sherman ◽  
Roman A. Novikov ◽  
Eugenia A. Levina ◽  
Sergey N. Kochetkov
Keyword(s):  
Transition Metal ◽  
Base Catalysis ◽  
Metal Free ◽  
Hydrazine Derivatives ◽  
Mild Conditions ◽  
Plausible Mechanism ◽  
Facile Route

A new reaction involving the quantitative coupling of phenolic substrates to azodicarboxylate esters under mild conditions is a facile route for obtaining hydrazine derivatives. A plausible mechanism, catalysts, scope and application are discussed.

C(sp2)–H functionalization of aldehyde-derived hydrazones via a radical process

2018 ◽  
Vol 16 (8) ◽  
pp. 1227-1241 ◽  
Author(s):  
Xiaoyan Xu ◽  
Jun Zhang ◽  
Hongguang Xia ◽  
Jie Wu
Keyword(s):  
Reaction Process ◽  
Radical Process ◽  
Mild Conditions ◽  
Recent Advances ◽  
Aminyl Radical

This review is focused on the recent advances in the C(sp2)–H functionalization of aldehyde-derived hydrazones via a radical process. Diverse substituted hydrazones including N-heterocycles are afforded under mild conditions with excellent selectivities. In general, an aminyl radical as the key intermediate is involved during the reaction process.

scholarly journals Simple and Efficient Synthesis of Allyl Sulfones through Cs2CO3-Mediated Radical Sulfonylation of Morita–Baylis–Hillman Adducts with Thiosulfonates

SynOpen ◽  
2021 ◽  
Vol 05 (01) ◽  
pp. 91-99
Author(s):  
Raju Jannapu Reddy ◽  
Angothu Shankar ◽  
Md. Waheed
Keyword(s):  
Efficient Synthesis ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Plausible Mechanism ◽  
High Yields

AbstractA highly efficient and eco-friendly method has been developed for the synthesis of allyl sulfones using Morita–Baylis–Hillman (MBH) adducts and thiosulfonates under mild conditions. The Cs2CO3-promoted radical sulfonylation provided a series of allyl sulfones in good to high yields with high stereoselectivities. A wide variety of MBH bromides/acetates as well as thiosulfonates were tolerated and reliable in scaled-up synthesis. A plausible mechanism is proposed to rationalize the radical sulfonylation.

Dimethyl Sulfoxide-Accelerated Reductive Deamination of Aromatic Amines with T-BuONO in Tetrahydrofuran

2018 ◽  
Vol 42 (11) ◽  
pp. 579-583
Author(s):  
Lu Fang ◽  
Liang Qi ◽  
Longfei Ye ◽  
Zhentao Pan ◽  
Wenjun Luo ◽  
...  
Keyword(s):  
Dimethyl Sulfoxide ◽  
Efficient Method ◽  
Aromatic Amines ◽  
One Pot ◽  
Mild Conditions ◽  
Aryl Amines ◽  
Plausible Mechanism

An efficient method for the conversion of aryl amines into arenes by a one-pot reductive deamination has been achieved. It was found the reductive deamination using t-BuONO in tetrahydrofuran could be accelerated by dimethyl sulfoxide and provided the deamination products with good yields under mild conditions. A plausible mechanism is discussed.

scholarly journals One-Pot Access to 2-Aryl-3-(arylmethyl)chromones

Synthesis ◽  
2019 ◽  
Vol 52 (06) ◽  
pp. 861-872
Author(s):  
Meng-Yang Chang ◽  
Kuan-Ting Chen ◽  
Yu-Lin Tsai ◽  
Han-Yu Chen
Keyword(s):  
Sodium Hydroxide ◽  
Aldol Condensation ◽  
One Pot ◽  
Mild Conditions ◽  
Efficient Transformation ◽  
Plausible Mechanism

Sodium hydroxide controlled intermolecular double aldol condensation of o-hydroxyacetophenones with 2 equivalents of aryl­aldehydes provides 2-aryl-3-(arylmethyl)chromones (a chimera of flavone and homoisoflavanone) in MeOH at 50 °C under mild conditions. The uses of various bases and solvents are investigated for one-pot facile and efficient transformation. A plausible mechanism is proposed.

Facile Domino Access to Unexpected Alkyl 3-Substituted-2-hydroxy-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylates

2013 ◽  
Vol 66 (8) ◽  
pp. 959 ◽  
Author(s):  
Ya-Ru Zhang ◽  
Xiao Huang ◽  
Dong-Cheng Xu ◽  
Jian-Wu Xie
Keyword(s):  
Air Oxidation ◽  
Dicarbonyl Compounds ◽  
Aerobic Conditions ◽  
Mild Conditions ◽  
Plausible Mechanism

A new domino alkylation–cyclization–air-oxidation of 2-halo-1,3-dicarbonyl compounds with 2-aminophenols promoted by caesium salts under aerobic conditions has been developed. Unexpected alkyl 3-substituted-2-hydroxy-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylates, rather than normal ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate, were exclusively obtained under mild conditions. A plausible mechanism for this unprecedented reaction is also given.

The Diorgano Dichalcogenides Addition to Benzyne under Mild Conditions

2007 ◽  
Author(s):  
Fabiano Toledo ◽  
Henrique Marques ◽  
João Comasseto ◽  
Cristiano Raminelli
Keyword(s):  
Mild Conditions
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