82044-44-8Relevant academic research and scientific papers
Sustainable Palladium-Catalyzed Tsuji-Trost Reactions Enabled by Aqueous Micellar Catalysis
Braga, Felipe C.,Gallou, Fabrice,Lee, Nicholas R.,Lippincott, Daniel J.,Lipshutz, Bruce H.,Moghadam, Farbod A.,Zhu, Bingchun
supporting information, (2020/07/15)
Palladium-catalyzed allylic substitution, or "Tsuji-Trost"reactions, can be run under micellar catalysis conditions featuring not only chemistry in water but also numerous combinations of reaction partners that require low levels of palladium, typically on the order of 1000 ppm (0.1 mol %). These couplings are further characterized by especially mild conditions, leading to a number of cases not previously reported in an aqueous micellar medium. Inclusion of diverse nucleophiles, such as N-H heterocycles, alcohols, dicarbonyl compounds, and sulfonamides is described. Intramolecular cyclizations further illustrate the broad utility of this process. In addition to recycling studies, a multigram scale example is reported, indicative of the prospects for scale up.
Aryltrifluoromethylative cyclization of unactivated alkenes by the use of PhICF3Cl under catalyst-free conditions
Guo, Jia,Xu, Cong,Liu, Xiaowei,Wang, Mang
, p. 2162 - 2168 (2019/02/27)
A concise and catalyst-free aryltrifluoromethylative cyclization of unactivated alkenes has been developed herein. The use of PhICF3Cl as a powerful trifluoromethylating agent allows easy transformations. A set of trifluoroethylated carbocycles and aza-hereocycles were efficiently synthesized in good yield and selectivity. A broad substrate scope, mild reaction conditions, and easy operation would make this method well-suited for applications.
Direct Allylation of Active Methylene Compounds with Allylic Alcohols by Use of Palladium/Phosphine-Borane Catalyst System
Shimizu, Aika,Hirata, Goki,Onodera, Gen,Kimura, Masanari
supporting information, p. 1954 - 1960 (2018/04/11)
The C?C bond formation between active methylene compounds and allylic alcohols has been newly developed by using a palladium complex as a catalyst together with a phosphine-borane ligand. The best phosphine-borane ligand for this direct allylation has bee
Photoredox Catalyzed Intramolecular Fluoroalkylarylation of Unactivated Alkenes
Zhang, Zuxiao,Martinez, Henry,Dolbier, William R.
, p. 2589 - 2598 (2017/03/14)
The first example of photoredox catalyzed difluoromethylation of unactivated alkenes coupled with C-C bond formation to an aryl ring is reported. The reactions are conducted under mild conditions and afford tetralin derivatives bearing difluoromethyl as well as other fluoroalkyl groups in good to high yields. In addition, the study indicates that 6-exo radical cyclization of an alkyl radical to a phenyl ring is faster than the respective 5-exo radical cyclization. A computational study provides insights to the experimental results.
Intramolecular formal [4+2] cycloaddition of 3-ethoxycyclobutanones and alkenes
Matsuo, Jun-Ichi,Sasaki, Shun,Hoshikawa, Takaya,Ishibashi, Hiroyuki
supporting information; scheme or table, p. 934 - 936 (2010/06/12)
Intramolecular formal [4+2] cycloaddition between 3-ethoxycyclobutanones and a carbon-carbon double bond to the corresponding bicyclo[4.n.0]alkan-2-one derivatives proceeded effectively by using ethylaluminium dichloride. The Royal Society of Chemistry 20
Catalytic deallylation of allyl- and diallylmalonates
Necas, David,Tursky, Matyas,Kotora, Martin
, p. 10222 - 10223 (2007/10/03)
Substituted allylmalonates undergo the selective C-C bond cleavage in the presence of triethylaluminum and a catalytic amount of nickel and ruthenium phosphine complexes, resulting in the loss of the allyl moiety and formation of monosubstituted malonates. Comparison of reactivity of the nickel and ruthenium complexes showed that the use of the former is general with respect to the structure of the substituted allylmalonates, and the activity of the latter depended on the substitution pattern of the double bond of the allylic moiety. The smooth deallylation may encourage the use of the allyl group as a protective group for the acidic hydrogen in malonates. Copyright
Et3B-promoted, Pd(0)-catalyzed allylation of active methylene compounds with allylic alcohols
Tamaru, Yoshinao,Horino, Yoshikazu,Araki, Misato,Tanaka, Shuji,Kimura, Masanari
, p. 5705 - 5709 (2007/10/03)
Triethylborane promotes the Pd(0)-catalyzed allylation of active methylene compounds (Meldrum's acid and malonates) with a variety of allylic alcohols. The reaction proceeds smoothly at room temperature and provides the allylation products in good yield. (C) 2000 Elsevier Science Ltd.
