Related Experiment Video
Updated: May 28, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Synthesis of Diastereomeric Hydrobenzofurans and Hydronaphthofurans via an Iodine Reagent-Promoted Intramolecular
Xinkun An1, Haoyun Ma1, Tingting Zhang1
1Innovation Center of Pesticide Research, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
Abstract:
The first metal- and base-free construction of diastereomeric hydrobenzofurans and hydronaphthofurans, which were capable of further transformations to achieve natural product frameworks, was achieved by the intramolecular oxidized dearomatization of phenol or naphthol derivatives via the promotion of iodine reagents. Enantioselective products were obtained through chiral substrates or iodine catalysts. This step-economical protocol built multiple chiral centers with extensive tolerance of various substrates, which resulted in a potential molecular library for developing functional polycyclic scaffolds.
More Related Videos
09:54Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
08:43Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
Alkynes 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.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Hydroboration-Oxidation of Alkenes