Related Experiment Video
Updated: Jan 27, 2026
A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
Published on: November 12, 2016
Consecutive intermolecular 1,1-carboboration reactions of Me3Si-substituted alkynes with the halogeno-B(C6F5)2
Karel Škoch1, Christophe Pauly, Constantin G Daniliuc
1Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstr. 40, 48149 Münster, Germany. erker@uni-muenster.de.
Abstract:
1-(Trimethylsilyl)propyne 2a reacts with halogenoboranes XB(C6F5)2 (X: Cl, Br) in a 1 : 1 molar ratio at r.t. to give the respective alkenylboranes 3. These undergo a subsequent 1,1-alkenylboration reaction with additional alkyne 2a to give the persubstituted 3-boryl-2,4-hexadiene products 4. The conjugated diyne bis(trimethylsilyl)butadiyne 2d reacts with ClB(C6F5)2 in a 2 : 1 molar ratio by a sequence of consecutive 1,1-carboboration reactions to give the persubstituted borylated octadiendiyne product 6.
More Related Videos
![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)
11:44Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
08:47Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
Published on: March 6, 2019
Related Concept Videos
02:28Intermolecular Forces in Solutions
When the strengths of the intermolecular forces of attraction between solute and solvent species in a solution are no different than those present in the separated components, the solution is formed with no accompanying energy change. Such a solution is called an ideal solution. A mixture of ideal gases (or gases such as helium and argon,...
03:13Intermolecular Forces
02:27Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
02:34Nucleophilic Substitution Reactions
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...
03:00Intermolecular vs Intramolecular Forces
01:38Preparation 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...