Electrochemical Nitroindolylation Bifunctionalization Reaction of Arylalkenes
Feng Zhang1, Xiangxi Liu1, Yi Yin1
1State Key Laboratory and Institute of Elemento-Organic Chemistry, National Engineering Research Center of Pesticide, College of Chemistry, Nankai University, Weijin Road 94#, Nankai District, Tianjin 300071, China.
None:
A novel electrochemical nitroindolylation bifunctionalization reaction of alkenes was developed. It was unprecedented that both C-C and C-N bonds were concurrently formed using sodium nitrite as the nitro free radical precursor in one pot. A series of α-aryl-β-nitroindole derivatives was generated in good to high yields. Moreover, a plausible mechanism for this bifunctionalization reaction of alkenes was proposed via a bromonitro intermediate in an SN2 pathway. In addition, ZCZ011, an expensive positive allosteric modulator of the cannabinoid CB1 receptor, was facilely synthesized using this method.
More Related Videos
10:10Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
Published on: July 28, 2018
08:12A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Related Concept Videos
01:20Electrophilic Aromatic Substitution: Nitration of Benzene
01:14Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
02:38Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
01:11Nucleophilic Aromatic Substitution: Elimination–Addition
01:30Nucleophilic 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...