1369331-61-2Relevant academic research and scientific papers
Organic chemistry: A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents
Qin, Tian,Cornella, Josep,Li, Chao,Malins, Lara R.,Edwards, Jacob T.,Kawamura, Shuhei,Maxwell, Brad D.,Eastgate, Martin D.,Baran, Phil S.
, p. 801 - 805 (2016/06/01)
Alkyl carboxylic acids are ubiquitous in all facets of chemical science, from natural products to polymers, and represent an ideal starting material with which to forge new connections. This study demonstrates how the same activating principles used for decades to make simple C-N (amide) bonds from carboxylic acids with loss of water can be used to make C-C bonds through coupling with dialkylzinc reagents and loss of carbon dioxide. This disconnection strategy benefits from the use of a simple, inexpensive nickel catalyst and exhibits a remarkably broad scope across a range of substrates (>70 examples).
Tandem ring-closing metathesis/transfer hydrogenation: Practical chemoselective hydrogenation of alkenes
Connolly, Timothy,Wang, Zhongyu,Walker, Michael A.,McDonald, Ivar M.,Peese, Kevin M.
supporting information, p. 4444 - 4447 (2015/01/09)
An operationally simple chemoselective transfer hydrogenation of alkenes using ruthenium metathesis catalysts is presented. Of great practicality, the transfer hydrogenation reagents can be added directly to a metathesis reaction and effect hydrogenation of the product alkene in a single pot at ambient temperature without the need to seal the vessel to prevent hydrogen gas escape. The reduction is applicable to a range of alkenes and can be performed in the presence of aryl halides and benzyl groups, a notable weakness of Pd-catalyzed hydrogenations. Scope and mechanistic considerations are presented.
A new approach to the synthesis of 1-oxaspiro[4.n]alkanes and tetrahydrofurans by the 1,5-CH insertion reaction of magnesium carbenoids
Satoh, Tsuyoshi,Yasoshima, Tsukasa,Momochi, Hitoshi
experimental part, p. 2074 - 2077 (2012/07/14)
1-Alkoxy-1-[2-chloro-2-(p-tolylsulfinyl)ethyl]cycloalkanes were prepared from various cyclic ketones in good overall yields. Treatment of these cycloalkanes bearing a sulfinyl group with i-PrMgCl resulted in the formation of 1-oxaspiro[4.n]alkanes in high to quantitative yields via the 1,5-CH insertion reaction of generated magnesium carbenoid intermediates. When this procedure was commenced with acyclic ketones, multi-substituted tetrahydrofurans were obtained in up to a 96% yield. This procedure provides a new and good way for the synthesis of 1-oxaspiro[4.n]alkanes and tetrahydrofurans with the formation of a carbon-carbon bond between a carbenoid carbon and a non-activated carbon in high yields. The oxygen atom in the magnesium carbenoid intermediates was proved to act very important roles in the 1,5-CH insertion reaction.
