74685-28-2

Upstream product

• 21433-46-5 lithium derivative from 1-decyne 
• 90791-90-5 Hexyl-bis-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borane 
• 111-85-3 n-chlorooctane 
• 629-05-0 n-octyne 
• 629-27-6 1-Iodooctane 
• 822-21-9 hexadec-7-yn-1-ol 
• 71091-89-9 n-octyl triflate 
• 111-87-5 octanol 
• 463-11-6 1-Fluoro-octane 
• 24608-03-5 Diethyl-(1-octin-1-yl)-aluminium 
• 111-83-1 1-bromo-octane 

Relevant academic research and scientific papers

Synthesis and characterization of soluble and n-dopable poly(quinoxaline vinylene)s and poly(pyridopyrazine vinylene)s with relatively small band gap

Synthesis and characterization of poly(quinoxaline vinylene)s and poly(pyridopyrazine vinylene)s with linear and branched aliphatic side chains are reported. The electron affinity of the polymers was measured with cyclic voltammetry (CV) and found to be h

N-Heterocyclic carbene copper-catalyzed direct alkylation of terminal alkynes with non-activated alkyl triflates

(NHC)-Cu-catalyzed C(sp)-C(sp3) bond formation has been successfully achieved under mild conditions. Nonactivated alkyl triflates, which could be easily derived from alcohols, were utilized as C-O electrophiles. Mechanistic studies suggested th

En Route to a Practical Primary Alcohol Deoxygenation

A long-standing scientific challenge in the field of alcohol deoxygenation has been direct catalytic sp3 C-O defunctionalization with high selectivity and efficiency, in the presence of other functionalities, such as free hydroxyl groups and amines widely present in biological molecules. Previously, the selectivity issue had been only addressed by classic multistep deoxygenation strategies with stoichiometric reagents. Herein, we propose a catalytic late-transition-metal-catalyzed redox design, on the basis of dehydrogenation/Wolff-Kishner (WK) reduction, to simultaneously tackle the challenges regarding step economy and selectivity. The early development of our hypothesis focuses on an iridium-catalyzed process efficient mainly with activated alcohols, which dictates harsh reaction conditions and thus limits its synthetic utility. Later, a significant advancement has been made on aliphatic primary alcohol deoxygenation by employing a ruthenium complex, with good functional group tolerance and exclusive selectivity under practical reaction conditions. Its synthetic utility is further illustrated by excellent efficiency as well as complete chemo- and regio-selectivity in both simple and complex molecular settings. Mechanistic discussion is also included with experimental supports. Overall, our current method successfully addresses the aforementioned challenges in the pertinent field, providing a practical redox-based approach to the direct sp3 C-O defunctionalization of aliphatic primary alcohols.

Nickel-catalyzed direct alkylation of terminal alkynes at room temperature: A hemilabile pincer ligand enhances catalytic activity

Direct coupling of alkyl halides with terminal alkynes provides an efficient and streamlined access to alkyl-substituted alkynes, which are important synthetic intermediates, biologically active molecules, and organic materials. However, until now,there h

Cross-coupling of nonactivated alkyl halides with alkynyl grignard reagents: A nickel pincer complex as the catalyst

In a pinch: The nickel pincer complex 1 catalyzes the cross-coupling of the title compounds with remarkable substrate scope and functional group tolerance. A nickel/alkynyl species was isolated and shown to be catalytically competent. THF=tetrahydrofuran, O-TMEDA=bis[2-(N,N-dimethylaminoethyl)] ether. Copyright

Ni-catalyzed Sonogashira coupling of nonactivated alkyl halides: Orthogonal functionalization of alkyl iodides, bromides, and chlorides

(Chemical Equation Presented) Ni-catalyzed Sonogashira coupling of nonactivated, β-H-containing alkyl halides, including chlorides, is reported. The coupling is tolerant to a wide range of functional groups, including ether, ester, amide, nitrile, keto, h

Conversion of a (sp3)C-F bond of alkyl fluorides to (sp 3)C-X (X = Cl, C, H, O, S, Se, Te, N) bonds using organoaluminium reagents

A simple method for the conversion of (sp3)C-F bonds of alkyl fluorides to (sp3)C-X (X = Cl, C, H, O, S, Se, Te, N) bonds has been achieved by the use of a hexane solution of organoaluminum reagents having Al-X bonds. The Royal Society of Chemistry.

Enantioselective Synthesis of Disubstituted Alkynes via Organoboranes

Iodine-induced rearrangement of the "ate" complex derived from diisopinocampheylalkylborane and various lithium acetylides furnishes optically active disubstituted alkynes with an enantiomeric excess comparable to that of the diisopinocampheylborane used in the initial asymmetric hydroboration.In the present investigation sec-butyldiisopinocampheylborane, prepared by asymmetric hydroboration of cis-2-butene with chiral diisopinocampheylborane of high enantiomeric excess, is used to yield sec-butyl-substituted alkynes in excellent (>=95percent) enantiomeric excess.Despite the statistical disadvantage of a 1:2 ratio of sec-butyl:isopinocampheyl groups, the desired alkyne is formed in 58percent yield by GLPC, compared to 38percent for the product derived from the migration of the isopinocampheyl group, thus suggesting low migratory aptitude for the latter.The iodine-induced rearrangement is highly stereospecific in nature and proceeds with complete retention of configuration at the migrating terminus.The method is capable of producing both enantiomers.