Reductions of esters, acyl halides, alkyl halides, and sulfonate esters with sodium borohydride in polyethylene glycols: scope and limitation of the reaction

1983 ◽  
Vol 48 (18) ◽  
pp. 3074-3077 ◽  
Author(s):  
Enzo Santaniello ◽  
Alberto Fiecchi ◽  
Ada Manzocchi ◽  
Patrizia Ferraboschi
Keyword(s):  
Sodium Borohydride ◽  
Alkyl Halides ◽  
Polyethylene Glycols ◽  
Acyl Halides

Nucleophile/Electrophile Combinations in Aromatic Substitution: From Wheland to Wheland–Meisenheimer Intermediates Using Strongly Activated Arenes

Synthesis ◽  
2017 ◽  
Vol 49 (15) ◽  
pp. 3347-3356 ◽  
Author(s):  
Gabriele Micheletti ◽  
Carla Boga
Keyword(s):  
Nitrogen Atom ◽  
Carbon Atom ◽  
Short Review ◽  
Alkyl Halides ◽  
Aryl Halides ◽  
Aromatic Substitution ◽  
Aromatic Carbon ◽  
Isolation And Characterization ◽  
Acyl Halides

This short review provides an overview on the interaction between 1,3,5-triaminobenzene derivatives and different kinds of electrophiles. Due to the ambident reactivity of these nucleophiles (i.e., at the nitrogen atom of the substituents and at the aromatic carbon atom) different compounds can be obtained. Particular attention is devoted to the detection, isolation, and characterization of covalent intermediates of aromatic substitution, starting from Wheland intermediates until the first detection and characterization of Wheland–Meisenheimer intermediates.1 Introduction2 Reactions between 1,3,5-Triaminobenzene Derivatives and Charged Electrophiles2.1 The Proton as an Electrophile2.2 Arenediazonium Salts as Electrophiles3 Reactions between 1,3,5-Triaminobenzene Derivatives and Neutral­ Electrophiles3.1 Alkyl Halides as Electrophiles3.2 Acyl Halides and Sulfonyl Chlorides as Electrophiles3.3 Aryl Halides and Heteroaryl Halides as Electrophiles3.4 Polynitroheteroaromatics as Electrophiles4 Conclusion

Intramolecular Radical Cyclization of Vinyl, Aryl and Alkyl Halides Using Catalytic Amount of Bis-tri-n-butyltin Oxide/Sodium Borohydride: A Novel Entry to Functionalized Carbocycles

Synlett ◽  
2015 ◽  
Vol 26 (08) ◽  
pp. 1055-1058 ◽  
Author(s):  
Namasivayam Palani ◽  
Sengottuvelan Balasubramanian ◽  
Tarur Dinesh
Keyword(s):  
Sodium Borohydride ◽  
Catalytic Amount ◽  
Radical Cyclization ◽  
Alkyl Halides ◽  
Cyclization Reactions

We wish to report a facile method in which a catalytic amount of bis-tri-n-butyltinoxide (TBTO) in the presence of sodium borohydride efficiently brings about the intramolecular radical cyclization of a variety of vinyl, aryl and alkyl halides to their corresponding functionalized bicyclic and tricyclic carbocycle frameworks. The methodology obviates the need for stoichiometric amounts of tin reagent normally required for radical cyclization reactions.

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