14213-84-4Relevant academic research and scientific papers
Transition Metal-Free sp3?sp3 Carbon-Carbon Coupling between Benzylboronic Esters and Alkyl Bromides
Barker, Timothy J.,Russell, Richard W.
supporting information, p. 2782 - 2784 (2021/06/25)
A transition metal-free coupling reaction of benzylboronic esters and alkyl halides has been developed. Both alkyl bromides and alkyl iodides were found to be competent substrates with the nucleophilic boronate intermediate generated from the combination of benzylboronic ester and an alkyllithium. Good chemoselectivity was observed for the reaction with the alkyl bromide in substrates with a second electrophile present. Both secondary and tertiary benzylboronic esters were effective nucleophiles in the reaction with primary alkyl halides. Mechanistic observations are consistent with a radical mechanism.
Site-Fixed Hydroboration of Terminal and Internal Alkenes using BX3/iPr2NEt**
Cui, Xin,Hu, Chenyang,Li, Sida,Liu, Liu Leo,Wu, Lipeng,Zhang, Jiong
supporting information, p. 26238 - 26245 (2021/11/09)
An unprecedented and general hydroboration of alkenes with BX3 (X=Br, Cl) as the boration reagent in the presence of iPr2NEt is reported. The addition of iPr2NEt not only suppresses alkene polymerizat
Development of unique dianionic Ir(III) CCC pincer complexes with a favourable spirocyclic NHC framework
Yan, Zhi-Bo,Dai, Kun-Long,Yang, Bin-Miao,Li, Zi-Hao,Tu, Yong-Qiang,Zhang, Fu-Min,Zhang, Xiao-Ming,Peng, Meng,Chen, Qi-Long,Jing, Ze-Ran
, p. 1761 - 1766 (2020/10/29)
A new type of dianionic Ir(III) CCC pincer complexes (SNHC-Ir, 1a-1c) is successfully designed and synthesized by developing a one-step methodology, which involves an initial coordination of Ir(I) with the NHC and subsequent metallation of double sp2C- H bonds. This method is considerably useful over those reported by using strong coordination ligand or carbonic anion exchange, and would provide an alternative efficient template of organometallics synthesis. Experimental and density functional theory (DFT) calculation results indicate that the spirocyclic framework is a favourable factor for the facile formation and stabilization of these complexes. Primary investigation shows that chloride 1b can well catalyze homo and hetero addition of styrene derivatives and remote olefin isomerization, which represents the first catalytic application of the dianionic CCC pincer complexes.
Stereoselective Rhodium-Catalyzed Isomerization of Stereoisomeric Mixtures of Arylalkenes
Yang, Hongxuan,Dong, Wenke,Wang, Wencan,Li, Tao,Zhao, Wanxiang
supporting information, p. 2833 - 2840 (2020/10/06)
A new efficient method for the synthesis of a high ratio of E -alkenes from E / Z mixtures of alkenes with B 2pin 2in the presence of a rhodium catalyst is described. This reaction features mild reaction conditions, broad functional group tolerance, and highly great application potential.
Enantio- and Regioselective NiH-Catalyzed Reductive Hydroarylation of Vinylarenes with Aryl Iodides
He, Yuli,Liu, Chuang,Yu, Lei,Zhu, Shaolin
supporting information, p. 21530 - 21534 (2020/10/02)
A highly enantio- and regioselective hydroarylation process of vinylarenes with aryl halides has been developed using a NiH catalyst and a new chiral bis imidazoline ligand. A broad range of structurally diverse, enantioenriched 1,1-diarylalkanes, a structure found in a number of biologically active molecules, have been obtained with excellent yields and enantioselectivities under extremely mild conditions.
Hoveyda–Grubbs catalysts with an N→Ru coordinate bond in a six-membered ring. Synthesis of stable, industrially scalable, highly efficient ruthenium metathesis catalysts and 2-vinylbenzylamine ligands as their precursors
Polyanskii, Kirill B.,Alekseeva, Kseniia A.,Raspertov, Pavel V.,Kumandin, Pavel A.,Nikitina, Eugeniya V.,Gurbanov, Atash V.,Zubkov, Fedor I.
supporting information, p. 769 - 779 (2019/04/17)
A novel and efficient approach to the synthesis of 2-vinylbenzylamines is reported. This involves obtaining 2-vinylbenzylamine ligands from tetrahydroisoquinoline by alkylation and reduction followed by the Hofmann cleavage. The resultant 2-vinylbenzyl-amines allowed us to obtain new Hoveyda–Grubbs catalysts, which were thoroughly characterised by NMR, ESIMS, and X-ray crystallography. The utility of this chemistry is further demonstrated by the tests of the novel catalysts (up to 10?2 mol %) in different metathesis reactions such as cross metathesis (CM), ring-closing metathesis (RCM) and ring-opening cross metathesis (ROCM).
Monothiolate ruthenium alkylidene complexes with tricyclic fluorinated N-heterocyclic carbene ligands
Akmalov, Timur R.,Masoud, Salekh M.,Vorobyeva, Daria V.,Dolgushin, Fedor M.,Nefedov, Sergey E.,Osipov, Sergey N.
, p. 38 - 40 (2019/02/19)
New monothiolate ruthenium alkylidene complexes bearing bulky tricyclic N-heterocyclic carbene ligands decorated with two geminal trifluoromethyl groups were synthesized. Their catalytic activity in representative olefin metathesis reactions, such as ring closing metathesis of diallyltosylamine and selfmetathesis of allylbenzene, has been evaluated.
Ruthenium-Alkylidene Complexes with Sterically Rigid Fluorinated NHC Ligands
Masoud, Salekh M.,Akmalov, Timur R.,Palagin, Konstantin A.,Dolgushin, Fedor M.,Nefedov, Sergey E.,Osipov, Sergey N.
supporting information, p. 5988 - 5996 (2018/11/10)
An efficient procedure for the preparation of novel olefin metathesis catalysts of Grubbs-Hoveyda type bearing sterically rigid NHC ligands has been developed. A preliminary evaluation of their catalytic activity has been performed on representative olefin metathesis reactions, such as RCM of malonates as well as self-metathesis of allylbenzene. As result, it was found that along with excellent robustness, new complexes demonstrate remarkable activity in metathesis of allylbenzene, outperforming commercially available Grubbs-Hoveyda catalyst in terms of yield and regioselectivity.
Oxygenation of Simple Olefins through Selective Allylic C?C Bond Cleavage: A Direct Approach to Cinnamyl Aldehydes
Liu, Jianzhong,Wen, Xiaojin,Qin, Chong,Li, Xinyao,Luo, Xiao,Sun, Ao,Zhu, Bencong,Song, Song,Jiao, Ning
supporting information, p. 11940 - 11944 (2017/09/20)
A novel metal-free allylic C?C σ-bond cleavage of simple olefins to give valuable cinnamyl aldehydes is reported. 1,2-Aryl or alkyl migration through allylic C?C bond cleavage occurs in this transformation, which is assisted by an alkyl azide reagent. This method enables O-atom incorporation into simple unfunctionalized olefins to construct cinnamyl aldehydes. The reaction features simple hydrocarbon substrates, metal-free conditions, and high regio- and stereoselectivity.
Unexpected formation of 1,4-diphenylbutylphosphinic acid from 1,4-diphenylbuta-1,3-diene and elemental phosphorus via the Trofimov–Gusarova reaction
Artem'ev, Alexander V.,Sutyrina, Anastasiya O.,Matveeva, Elena A.,Albanov, Alexander I.,Klyba, Lyudmila V.
, p. 137 - 138 (2017/03/30)
trans,trans-1,4-Diphenylbuta-1,3-diene reacts with elemental (red) phosphorus in the superbasic KOH / DMSO (H2O) system (120?°C, 3 h) to give, after acidic work-up, 1,4-diphenylbutylphosphinic acid in 48% yield.
