77566-29-1

Upstream product

• 34886-50-5 (5-iodopent-1-yn-1-yl)benzene 
• 75-04-7 ethylamine 
• 5390-04-5 pent-1-yn-5-ol 
• 24595-58-2 5-phenylpent-4-yn-1-ol 
• 557-66-4 ethanamine hydrochloride 
• 591-50-4 iodobenzene 

Downstream Products

• 77566-33-7 N-chloro N-ethyl phenyl-5 pentyne-4 yl amine 
• 1620229-41-5 N-ethyl-5-phenylpent-4-yn-1-sulfamoyl azide 
• 1620229-42-6 2-ethyl-5-(phenylethynyl)-1,2,6-thiadiazinane 1,1-dioxide 

Relevant academic research and scientific papers

Chemoselective amination of propargylic C(sp3)-H bonds by cobalt(II)-based metalloradical catalysis

Highly chemoselective intramolecular amination of propargylic C(sp 3)-H bonds has been demonstrated for N-bishomopropargylic sulfamoyl azides through cobalt(II)-based metalloradical catalysis. Supported by D 2h-symmetric amidoporphyrin ligand 3,5-DitBu-IbuPhyrin, the cobalt(II)-catalyzed C-H amination proceeds effectively under neutral and nonoxidative conditions without the need of any additives, and generates N 2 as the only byproduct. The metalloradical amination is suitable for both secondary and tertiary propargylic C-H substrates with an unusually high degree of functional-group tolerance, thus providing a direct method for high-yielding synthesis of functionalized propargylamine derivatives. Make a ring of it: Highly chemoselective intramolecular amination of propargylic C(sp3)-H bonds has been achieved with a high degree of functional-group tolerance through the title reaction. The [Co(P1)]-catalyzed C-H amination proceeds under neutral and nonoxidative conditions without the need of any additives, thus providing a direct method for efficient synthesis of functionalized propargylamine derivatives with N2 as the only by-product.

Preparations et essais d'heterocyclisation radicalaire de nitrites et N-chloroamines acetyleniques

Nitrites RCC(CH2)nONO and N-chloroamines RCC(CH2)nN(Et)Cl (n = 3,4; R = H,Ph,Me) have been treated so as to form the corresponding heteroatomic radicals.In the case of nitrites, a product resulting from intramolecular addition of the alkoxy radical to the triple bond could be isolated only for n = 3.This product, which was obtained with a very poor yield, is the γ-butyrolactone resulting from decomposition of a primary product not isolated.When n = 4 and R = H, an isoxazole which could derive from an initial step consisting of the intramolecular abstraction of a propargylic hydrogen was formed.With acetylenic N-chloramines, we could not identify any product resulting from intramolecular addition of an aminyl radical to the triple bond.These rather poor synthetic results are compared to the much better ones obtained by intramolecular addition of the thiyl radical to the acetylenic system, and the origin of this difference in behaviour is discussed.