Related Experiment Video
Updated: Aug 21, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Rh-catalyzed regio-switchable cross-coupling of gem-difluorinated cyclopropanes with allylboronates to structurally
Yaxin Zeng1, Hui Yang1, Jiayi Du1
1West China School of Public Health and West China Fourth Hospital, West China-PUMC C.C. Chen Institute of Health, and State Key Laboratory of Biotherapy, Sichuan University Chengdu 610041 China xiayingscu@scu.edu.cn.
Abstract:
The control of linear/branched selectivity is one of the major focuses in transition-metal catalyzed allyl-allyl cross-coupling reactions, in which bond connection occurs at the terminal site of both the allyl fragments forming different types of 1,5-dienes. Herein, terminal/internal regioselectivity is investigated and found to be switchable in allyl-allyl cross-coupling reactions between gem-difluorinated cyclopropanes and allylboronates. The controlled terminal/internal regioselectivity arises from the fine-tuning of the rhodium catalytic system. Fluorinated 1,3-dienes, 1,4-dienes and 1,5-dienes are therefore produced in good yields with respectively isomerized terminal, internal, and terminal regioselectivity.
More Related Videos
07:36Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
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...
Cycloaddition Reactions: Overview
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.