Access to Five-Membered Silacycles via Pd-Catalyzed Heck-Type Coupling with Arylthianthrenium Salts
Jia-Quan Wang1,2, Ze-Dong Li2, Xiao-Xue Nie2
1School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, P. R. China.
None:
Here, we report the preparation of a series of dihydrosilole derivatives via a Pd-catalyzed Heck-type reaction by employing arylthianthrenium salts as the arylating reagent. The reaction features mild conditions, excellent functional group and heterocycle tolerance, thus providing a general approach for the construction of 2,3-dihydrosiloles in high efficiency. Notably, the new protocol could be further applied to the late-stage installation of silacycles in bioactive complexes via site-selective thianthrenation and a sequential Pd-catalyzed Heck-type coupling reaction.
More Related Videos
Related Concept Videos
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Electrophilic 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.
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)

