3721-95-7Relevant articles and documents
Cobalt-Catalyzed Acceptorless Dehydrogenation of Alcohols to Carboxylate Salts and Hydrogen
Gunanathan, Chidambaram,Kishore, Jugal,Pattanaik, Sandip,Pradhan, Deepak Ranjan
supporting information, (2020/03/03)
The facile oxidation of alcohols to carboxylate salts and H2 is achieved using a simple and readily accessible cobalt pincer catalyst (NNNHtBuCoBr2). The reaction follows an acceptorless dehydrogenation pathway and displays good functional group tolerance. The amine-amide metal-ligand cooperation in cobalt catalyst is suggested to facilitate this transformation. The mechanistic studies indicate that in-situ-formed aldehydes react with a base through a Cannizzaro-type pathway, resulting in potassium hemiacetolate, which further undergoes catalytic dehydrogenation to provide the carboxylate salts and H2
Synthesis method of analgesic intermediate bromomethyl cyclobutane
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Paragraph 0009; 0010; 0011; 0012; 0013; 0014, (2017/07/21)
The invention relates to a synthesis method of analgesic intermediate bromomethyl cyclobutane. The synthesis method comprises the following steps: by taking ethylene and acrylic acid as starting materials, carrying out Diels-Alder reaction to obtain cyclobutanecarboxylic acid, then reducing to obtain cyclobutanemethanol, and then brominating to obtain high-purity bromomethyl cyclobutane, wherein the total yield reaches more than 65%. The synthesis method provided by the invention has the advantages of available raw materials, mild reaction conditions, simple postprocessing operation, small environmental pollution, short reaction time, high reaction operational safety, high reaction yield, good product quality and low cost, and industrial production is facilitated.
Gold-catalyzed cycloisomerization of 1,7-enyne esters to structurally diverse cis -1,2,3,6-tetrahydropyridin-4-yl ketones
Rao, Weidong,Sally,Koh, Ming Joo,Chan, Philip Wai Hong
, p. 3183 - 3195 (2013/06/27)
A synthetic method that relies on gold(I)-catalyzed cycloisomerization of 1,7-enyne esters to prepare highly functionalized cis-1,2,3,6-tetrahydropyridin- 4-yl ketone derivatives in good to excellent yields and as a single regio-, diastereo-, and enantiomer is described. By taking advantage of the distinctive differences in the electronic and steric properties between an NHC (NHC = N-heterocyclic carbene) and phosphine ligand in the respective gold(I) complexes, a divergence in product selectivity was observed. In the presence of [PhCNAuIPr]+SbF6- (IPr = 1,3-bis(2,6- diisopropylphenyl)imidazol-2-ylidine) as the catalyst, tandem 1,3-acyloxy migration/6-exo-trig cyclization/1,5-acyl migration of the substrate was found to selectively occur to give the δ-diketone-substituted 1,2,3,6-tetrahydropyridine adduct. In contrast, reactions with the gold(I) phosphine complex [MeCNAu(JohnPhos)]+SbF6- (JohnPhos = (1,1′-biphenyl-2-yl)-di-tert-butylphosphine) as the catalyst was discovered to result in preferential 1,3-acyloxy migration/6-exo-trig cyclization/hydrolysis of the 1,7-enyne ester and formation of the cis-1,2,3,6-tetrahydropyridin-4-yl ketone derivative. The utility of this piperidine forming strategy as a synthetic tool that makes use of 1,7-enyne esters was exemplified by its application to the synthesis of an enantiopure analogue of the bioactive 2,3,4,4a,5,9b-hexahydroindeno[1,2-c]pyridine family of compounds.
