71271-16-4Relevant academic research and scientific papers
Photocatalytic acylarylation of unactivated alkenes with diaryliodonium salts toward indanones and related compounds
Chen, Yongtao,Shu, Chenyun,Luo, Fang,Xiao, Xiaohui,Zhu, Gangguo
, p. 5373 - 5376 (2018)
A novel photocatalytic acylarylation of unactivated alkenes using diaryliodonium salts as the arylation reagent is described. The reaction produces a variety of 2-benzyl indanones, 3,4-dihydronaphthalen-1(2H)-ones, and 2,3-dihydroquinolin-4(1H)-ones in pr
Enantioselective Intramolecular Hydroacylation of Unactivated Alkenes: An NHC-Catalyzed Robust and Versatile Formation of Cyclic Chiral Ketones
Janssen-Müller, Daniel,Schedler, Michael,Fleige, Mirco,Daniliuc, Constantin G.,Glorius, Frank
supporting information, p. 12492 - 12496 (2015/10/12)
A highly enantioselective intramolecular N-heterocyclic carbene (NHC)-catalyzed hydroacylation reaction gives access to a range of cyclic ketones from unactivated olefin-substituted aldehydes (up to 99% ee). Remarkably, aliphatic aldehydes were also transformed efficiently in an NHC-catalyzed hydroacylation reaction for the first time. 100% Organic: A highly enantioselective N-heterocyclic carbene (NHC)-catalyzed intramolecular hydroacylation of aromatic and, more interestingly, aliphatic aldehydes with unactivated olefins offers access to a range of cyclic α-chiral ketones bearing quaternary centers. The reaction was found to be highly robust and proceeds with excellent yield in the presence of a diverse range of functional groups.
Intramolecular palladium-catalyzed alkane C-H arylation from aryl chlorides
Rousseaux, Sophie,Davi, Michael,Sofack-Kreutzer, Julien,Pierre, Cathleen,Kefalidis, Christos E.,Clot, Eric,Fagnou, Keith,Baudoin, Olivier
supporting information; experimental part, p. 10706 - 10716 (2010/09/17)
The first examples of efficient and general palladium-catalyzed intramolecular C(sp3)-H arylation of (hetero)aryl chlorides, giving rise to a variety of valuable cyclobutarenes, indanes, indolines, dihydrobenzofurans, and indanones, are described. The use of aryl and heteroaryl chlorides significantly improves the scope of C(sp3)-H arylation by facilitating the preparation of reaction substrates. Careful optimization studies have shown that the palladium ligand and the base/solvent combination are crucial to obtaining the desired class of product in high yields. Overall, three sets of reaction conditions employing PtBu3, PCyp3, or PCy3 as the palladium ligand and K 2CO3/DMF or Cs2CO3/pivalic acid/mesitylene as the base/solvent combination allowed five different classes of products to be accessed using this methodology. In total, more than 40 examples of C-H arylation have been performed successfully. When several types of C(sp3)-H bond were present in the substrate, the arylation was found to occur regioselectively at primary C-H bonds vs secondary or tertiary positions. In addition, in the presence of several primary C-H bonds, selectivity trends correlate with the size of the palladacyclic intermediate, with five-membered rings being favored over six- and seven-membered rings. Regio- and diastereoselectivity issues were studied computationally in the prototypal case of indane formation. DFT(B3PW91) calculations demonstrated that C-H activation is the rate-determining step and that the creation of a C-H agostic interaction, increasing the acidity of a geminal C-H bond, is a critical factor for the regiochemistry control.
New, practical and effective sources of fluoride ion for desilylation to form carbon anions
Busch-Petersen, Jakob,Bo, Yunxin,Corey
, p. 2065 - 2068 (2007/10/03)
Suspensions of powdered glassy solids prepared by fusion of 1:1 mixtures of CsF-CsOH and CsF-CsCl effectively catalyze the generation of enolates, acetylide and other anions from trimethylsilylated precursors.
