scholarly journals Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis

2016 ◽  
Vol 3 (5) ◽  
pp. 160102 ◽  
Author(s):  
Sadayuki Arimori ◽  
Okiya Matsubara ◽  
Masahiro Takada ◽  
Motoo Shiro ◽  
Norio Shibata
Keyword(s):  
Copper Catalysis ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Keto Esters ◽  
Wide Range ◽  
Allyl Alcohols ◽  
High Yields ◽  
Iodonium Ylides

Difluoromethanesulfonyl hypervalent iodonium ylides 2 were developed as electrophilic difluoromethylthiolation reagents for a wide range of nucleophiles. Enamines, indoles, β-keto esters, silyl enol ethers and pyrroles were effectively reacted with 2 affording desired difluoromethylthio (SCF 2 H)-substituted compounds in good to high yields under copper catalysis. The reaction of allyl alcohols with 2 under the same conditions provided difluoromethylsulfinyl (S(O)CF 2 H) products in good yields. The difluoromethylthiolation of enamines is particularly effective with wide generality, thus the enamine method was nicely extended to the synthesis of a series of difluoromethythiolated cyclic and acyclic β-keto esters, 1,3-diketones, pyrazole and pyrimidine derivatives by a consecutive, two-step one-pot reaction using 2.

scholarly journals One-Pot Synthesis of Silylated Enol Triflates from Silyl Enol Ethers for Cyclohexynes and 1,2-Cyclohexadienes

2018 ◽  
Vol 2018 (25) ◽  
pp. 3343-3347 ◽  
Author(s):  
Kazuki Inoue ◽  
Ryo Nakura ◽  
Kentaro Okano ◽  
Atsunori Mori
Keyword(s):  
One Pot ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
One Pot Synthesis

Synthesis of Chlorinated Arenes and Hetarenes by One-Pot Cyclizations of 1,3-Bis-silyl Enol Ethers

Synlett ◽  
2019 ◽  
Vol 30 (06) ◽  
pp. 665-673 ◽  
Author(s):  
Peter Langer ◽  
Zahid Hassan
Keyword(s):  
Cost Effective ◽  
Coupling Reactions ◽  
One Pot ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Cross Coupling Reactions ◽  
Silyl Enol Ether ◽  
Synthetic Routes ◽  
Metal Catalyzed ◽  
High Level

This account describes our recent findings and progress in synthesizing chlorinated arenes and hetarenes by one-pot cyclizations of 1,3-bis-silyl enol ether derivatives. These reactions allow for the preparation of highly functionalized products with a high level of regioselectivity. The synthetic routes are cost-effective avoiding additional functionalization steps. The products are difficult to be accessed by other methods. The chlorine atom is of relevance in medicinal and agriculture chemistry. In addition, it allows further functionalizations by transition-metal-catalyzed cross-coupling reactions.1 Introduction2 Cyclizations of 2-Chloro-1,3-bis(silyloxy)-1,3-butadienes2.1 3,5-Dihydroxychlorophthalates2.2 2,4-Dihydroxy-homochlorophthalates2.3 2-(Arylsulfonyl)chloropyridines2.4 1-Azaxanthones3 Cyclizations of 4-Chloro-1,3-bis(trimethylsilyloxy)-1,3-butadienes3.1 3-Chlorosalicylates3.2 Functionalized Chlorobiaryls3.3 3-Chloro-5-(2-chloroethyl)-salicylates3.4 2,4-Dihydroxychlorobenzophenones4 Cyclizations of 2-Chloro-3-(silyloxy)-2-en-1-ones4.1 Functionalized Chlorophenols4.2 Functionalized Chlorinated Biaryls and Chlorofluorenones4.3 Functionalized Chlorochromenones4.4 Functionalized 3-(Methylthio)chlorophenols4.5 Functionalized 3-Chloromethylphenols5 Conclusions6 List of Abbreviations

A Green Approach for the Synthesis of Novel 7,11-Dihydro-6H-chromeno[3,4-e]isoxazolo[5,4-b]pyridin-6-one Derivatives Using Acidic Ionic Liquid [C4mim][HSO4]

2016 ◽  
Vol 69 (9) ◽  
pp. 1049 ◽  
Author(s):  
Sudesh Kumari ◽  
M. Rajeswari ◽  
Jitender M. Khurana
Keyword(s):  
Ionic Liquid ◽  
Crystal Packing ◽  
Aromatic Aldehydes ◽  
Green Solvent ◽  
One Pot ◽  
X Ray ◽  
Acidic Ionic Liquid ◽  
Green Approach ◽  
Wide Range ◽  
High Yields

A multicomponent reaction capable of affording a wide range of novel 7,11-dihydro-6H-chromeno[3,4-e]isoxazolo[5,4-b]pyridin-6-one derivatives via one-pot three-component condensation of 4-hydroxycoumarin, aromatic aldehydes, and 5-amino-3-methylisoxazole in ionic liquid 1-butyl-3-methylimidazolium hydrogen sulfate ([C4mim][HSO4]) is reported. Structures have been confirmed by spectral and X-ray studies. Crystal packing of 4b has also been reported. Green solvent, short reaction time, easy workup, and high yields are the salient features of the present protocol.

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