709-12-6Relevant articles and documents
Nickel-catalyzed Heck reaction of cycloalkenes using aryl sulfonates and pivalates
Zhou, Jianrong Steve,Huang, Xiaolei,Teng, Shenghan,Chi, Yonggui Robin
supporting information, p. 3933 - 3936 (2021/04/26)
Nickel-catalyzed Heck reaction of cycloalkenes delivers unusual conjugated arylated isomers. Nickel(0) catalysts ligated by chelating dialkylphosphines effectively activate not only aryl triflates as electrophiles, but also less reactive aryl mesylates, t
Regiodivergent DH or HD Addition to Alkenes: Deuterohydrogenation versus Hydrodeuterogenation
Hilt, Gerhard,Li, Luomo
supporting information, (2020/03/03)
The regioselective and regiodivergent addition of H-D to a variety of 1,1-diarylalkenes was realized utilizing selectively deuterated dihydroaromatic compounds, which were generated by cobalt catalysis. The reaction was initiated by catalytic amounts of B
Enantioselective Copper Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution
Liu, En-Chih,Topczewski, Joseph J.
, p. 5135 - 5138 (2019/03/29)
The copper(I) catalyzed alkyne-azide cycloaddition (CuAAC), a click reaction, is one of the most powerful catalytic reactions developed during the last two decades. Conducting CuAAC enantioselectively would add a third dimension to this reaction and would
Cyclopentene Annulations of Alkene Radical Cations with Vinyl Diazo Species Using Photocatalysis
Sarabia, Francisco J.,Li, Qiankun,Ferreira, Eric M.
supporting information, p. 11015 - 11019 (2018/07/30)
A direct (3+2) cycloaddition between alkenes and vinyl diazo reagents using either Cr or Ru photocatalysis is described. The intermediacy of a radical cation species enables a nucleophilic interception by vinyl diazo compounds, a departure from their trad
Gold catalyzed Heck-coupling of arenediazonium o-benzenedisulfonimides
Barbero, Margherita,Dughera, Stefano
, p. 295 - 301 (2018/01/12)
Diazonium salts, and precisely arenediazonium o-benzenedisulfonimides, have been used for the first time as efficient electrophilic partners in gold catalyzed Heck-coupling reactions. The synthetic protocol was general, easy and gave the target products in satisfactory yields. Mechanistic insights revealed the fundamental roles of the o-benzenedisulfonimide anion as an electron transfer agent thath promotes a radical pathway that does not require the presence of photocatalysts or external oxidants.
Regio- and enantioselective Baeyer-Villiger oxidation: Kinetic resolution of racemic 2-substituted cyclopentanones
Zhou, Lin,Liu, Xiaohua,Ji, Jie,Zhang, Yuheng,Wu, Wangbin,Liu, Yangbin,Lin, Lili,Feng, Xiaoming
, p. 3938 - 3941 (2014/08/18)
A kinetic resolution of racemic 2-substituted cyclopentanones via highly regio- and enantioselective Baeyer-Villiger oxidation has been successfully developed. The reaction could afford the normal 6-substituted δ-lactones in up to 98% ee and >19/1 regioselectivity. Meanwhile, the unreacted ketones were recovered in excellent ee values (up to 98%). It represents the best results of the kinetic resolution of racemic 2-substituted cyclopentanones via nonenzymic asymmetric BV oxidation.
Controlling olefin isomerization in the heck reaction with neopentyl phosphine ligands
Lauer, Matthew G.,Thompson, Mallory K.,Shaughnessy, Kevin H.
, p. 10837 - 10848 (2015/01/08)
The use of neopentyl phosphine ligands was examined in the coupling of aryl bromides with alkenes. Di-tert-butylneopentylphosphine (DTBNpP) was found to promote Heck couplings with aryl bromides at ambient temperature. In the Heck coupling of cyclic alkenes, the degree of alkene isomerization was found to be controlled by the choice of ligand with DTBNpP promoting isomerization to a much greater extent than trineopentylphosphine (TNpP). Under optimal conditions, DTBNpP provides high selectivity for 2-aryl-2,3-dihydrofuran in the arylation of 2,3-dihydrofuran, whereas TNpP provided high selectivity for the isomeric 2-aryl-2,5-dihydrofuran. A similar complementary product selectivity is seen in the Heck coupling of cyclopentene. Heck coupling of 2-bromophenols or 2-bromoanilides with 2,3-dihydrofurans affords 2,5-epoxybenzoxepin and 2,5-epoxybenzazepins, respectively.
Selective arylation at the vinylic site of cyclic olefins
Wu, Xiaojin,Zhou, Jianrong
supporting information, p. 4794 - 4796 (2013/06/05)
Cyclic olefins usually give Heck products having an aryl ring residing at the allylic or homoallylic position. We describe herein a new method that allows arylation at the vinylic position of various cyclic olefins.
Achieving vinylic selectivity in Mizoroki-heck reaction of cyclic olefins
Wu, Xiaojin,Lu, Yunpeng,Hirao, Hajime,Zhou, Jianrong
, p. 6014 - 6020 (2013/06/26)
In Heck reactions of cyclic olefins, the products usually have aryl groups that end up at the allylic and/or homoallylic position. We herein report new selectivity that adds aryl groups to the vinylic position. Cyclic olefins of various ring size worked well. The desired isomers were produced by palladium-hydride-catalyzed isomerization of the initial products. Thus, a specific catalyst must be used so that it can perform two jobs under one set of reaction conditions. Copyright
Kumada coupling of aryl, heteroaryl, and vinyl chlorides catalyzed by amido pincer nickel complexes
Liu, Ning,Wang, Zhong-Xia
experimental part, p. 10031 - 10038 (2012/02/05)
A series of amido pincer complexes of nickel were examined for their catalysis in the Kumada cross-coupling reaction. The P,N,O-pincer nickel complexes tested are active catalysts for the cross-coupling of aryl, heteroaryl, and vinyl chlorides with aryl Grignard reagents. The reactions can proceed at room temperature and tolerate functional groups in aryl chlorides with the aid of LiCl and ZnCl2 additives (Figure presented).
