95391-00-7Relevant academic research and scientific papers
An acid-catalyzed formal allylic C-H oxidation of aryl cycloalkenes with N-propylthiosuccinimide
Huang, Deshun,Wang, Haining,Guan, Huan,Huang, Hu,Shi, Yian
, p. 1548 - 1551 (2011/05/03)
A mild acid-catalyzed formal allylic C-H oxidation of aryl cycloalkenes with N-propylthiosuccinimide in the presence of various nucleophiles to generate allylic ethers, esters, and sulfonamides is described. A possible reaction mechanism has been proposed.
Functionalization of unactivated alkenes through iridium-catalyzed borylation of carbon-hydrogen bonds. Mechanism and synthetic applications
Olsson, Vilhelm J.,Szabo, Kalman J.
supporting information; experimental part, p. 7715 - 7723 (2010/02/28)
(Chemical Equation Presented) This paper describes an efficient carbon-carbon bond formation reaction, which is based on carbon-hydrogen bond functionalization of unactivated alkenes. This process is based on in situ generation of allylic and vinylic boronates by iridium-catalyzed borylation of alkenes followed by carbon-carbon bond formation reactions. The selectivity of the carbon-hydrogen bond functionalization can be efficiently controlled for cyclic alkenes. By using additives, such as methylimidazole and DBU, the iridium-catalyzed borylation led to formation of allyl boronates, which reacted with aldehydes in a one-pot sequence affording stereodefined homoallylic alcohols. Cycloalkenes without additives aswell as acyclic substrates gave vinylic boronates, which were coupled with organohalides in a Suzuki-Miyaura sequence. By this process allylic and vinylic silabutadiene derivatives can be prepared from allylsilanes with excellent regio- and stereoselectivity. The mechanism of the carbon-hydrogen bond functionalization based on the borylation reaction was explored by isotope labeling experiments, measuring the kinetic isotope effect and study of the effects of the additives on the selectivity of the process. It was concluded that the reactions proceed via a dehydrogenative borylationmechanism,which shows analogous features with the palladium-catalyzed Heck coupling reaction.
Cyclohexynes as intermediates in a novel endo-cyclization of alkynylzincates derived from 5-hexynyl tosylates
Harada, Toshiro,Otani, Takeshi,Oku, Akira
, p. 2855 - 2858 (2007/10/03)
The n-type endo-cyclization of metal acetylides to form cyclohexynes was observed for the first time in the reaction of alkynylzincates derived from 5-hexynyl tosylates. The endo-cyclization took place in competition with erocyclization, leading to the formation of 1-(cyclopentylidene)alkylzincs.
