Hydroboration of terminal alkenes and trans-1,2-diboration of terminal alkynes catalyzed by a Mn(I) alkyl complex

AbstractAsymmetric hydroboration of simple and unactivated terminal alkenes (α-olefins), feedstock chemicals derived from the petrochemical industry, has not been efficiently realized for past decades. Using a bulky ANIPE ligand, we achieved a rare example of highly enantioselective copper-catalyzed Markovnikov hydroboration of α-olefins. The chiral secondary alkylboronic ester products were obtained in moderate to good yields and regioselectivities with excellent enantioselectivities.1 Introduction2 Conditions Optimization3 Substrate Scope4 Application5 Mechanistic Discussion6 Conclusions and Future Directions

Download Full-text

Thioether-Facilitated Iridium-Catalyzed Hydrosilylation of Steric 1,1-Disubstituted Olefins

10.26434/chemrxiv.9859103.v1 ◽

2019 ◽

Author(s):

Shengtao Ding

Keyword(s):

Side Chains ◽

Feasible Method ◽

Iridium Catalysis ◽

Efficient Strategy ◽

Terminal Alkenes ◽

And Control ◽

Sulfur Containing ◽

Organosilicon Polymers

One facile and efficient strategy for the hydrosilylation of steric 1,1-disubstituted terminal alkenes is demonstrated. Investigations on substrate scope and control experiments revealed the necessity of thioether in promoting this process under a simple iridium catalysis system. This convenient and feasible method is expected to be useful in the synthesis of sulfur-containing organosilicon polymers with different side-chains.

Download Full-text

Indium(III) Catalyzed Direct sp3-sp C-C Bond Formation from Alcohols and Terminal Alkynes

Letters in Organic Chemistry ◽

10.2174/1570178611310080004 ◽

2013 ◽

Vol 10 (8) ◽

pp. 555-561 ◽

Cited By ~ 5

Author(s):

Guangming Nan ◽

Jun Zhou

Keyword(s):

Bond Formation ◽

Terminal Alkynes

Download Full-text

Transition Metal-Catalyzed Carboxylation of Terminal Alkynes with CO2

Mini-Reviews in Organic Chemistry ◽

10.2174/1570193x15666180101150819 ◽

2018 ◽

Vol 15 (4) ◽

pp. 283-290 ◽

Cited By ~ 8

Author(s):

Chang Qiao ◽

Yu Cao ◽

Liang-Nian He

Keyword(s):

Transition Metal ◽

Terminal Alkynes ◽

Transition Metal Catalyzed ◽

Metal Catalyzed

Download Full-text

Synthesis of Novel 1,2,3-Triazole Derivatives of Isocoumarins and 3,4-Dihydroisocoumarin with Potential Antiplasmodial Activity In Vitro

Medicinal Chemistry ◽

10.2174/1573406416666200602161047 ◽

2020 ◽

Vol 16 ◽

Author(s):

Lucas da Silva Santos ◽

Matheus Fillipe Langanke de Carvalho ◽

Ana Claudia de Souza Pinto ◽

Amanda Luisa da Fonseca ◽

Julio César Dias Lopes ◽

...

Keyword(s):

Triazole Ring ◽

Antiplasmodial Activity ◽

World Health ◽

Dipolar Cycloaddition ◽

Terminal Alkynes ◽

The World ◽

Ic50 Values ◽

Derivatives Of ◽

Active Substances

Background: Malaria greatly affects the world health, having caused more than 228 million cases only in 2018. The emergence of drug resistance is one of the main problems in its treatment, demonstrating the urge for the development of new antimalarial drugs. Objective: Synthesis and in vitro antiplasmodial evaluation of triazole compounds derived from isocoumarins and a 3,4- dihydroisocoumarin. Method: The compounds were synthesized in 4 to 6-step reactions with the formation of the triazole ring via the Copper(I)-catalyzed 1,3-dipolar cycloaddition between isocoumarin or 3,4-dihydroisocoumarin azides and terminal alkynes. This key reaction provided compounds with an unprecedented connection of isocoumarin or 3,4-dihydroisocoumarin and the 1,2,3-triazole ring. The products were tested for their antiplasmodial activity against a Plasmodium falciparum chloroquine resistant and sensitive strains (W2 and 3D7, respectively). Results: Thirty-one substances were efficiently obtained by the proposed routes with an overall yield of 25-53%. The active substances in the antiplasmodial test displayed IC50 values ranging from 0.68-2.89 μM and 0.85-2.07 μM against W2 and 3D7 strains, respectively.

Download Full-text