Protecting group free synthesis of 6-substituted naphthols and binols
Daniela Verga1, Claudia Percivalle, Filippo Doria
1Dipartimento di Chimica Organica, Università di Pavia, V.le Taramelli 10, 27100 Pavia, Italy. danielaverga@gmail.com
Abstract:
A straightforward route for the preparation of 6-substituted naphthols and 6,6'-disubstituted binols (binol = 2,2'-dihydroxy-1,1'-binaphthyl) is presented. The synthesis has been accomplished by a one-step procedure starting from 6-bromo derivatives via direct lithiation with n-BuLi, followed by the addition of several electrophiles. This C-C functionalization has been successfully achieved with iodomethane, 3-methoxybenzaldehyde, benzophenone, methyl-2-methylbenzoate, methylbenzoate, dimethyl carbonate, ethyl 2-chloro-2-oxoacetate, and 2,2-dimethyloxirane (E). This reactivity offers a useful protecting group free synthetic protocol, toward chiral disubstituted 6,6'-binols with configuration retention of the binol moiety.
More Related Videos
Related Concept Videos
Protection of Alcohols
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...
Protecting Groups for Aldehydes and Ketones: Introduction
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
Nucleophilic Aromatic Substitution: Elimination–Addition
Preparation of Alcohols via Substitution Reactions
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between the...


