78604-62-3Relevant academic research and scientific papers
Iron-catalysed enantioconvergent Suzuki-Miyaura cross-coupling to afford enantioenriched 1,1-diarylalkanes
Tyrol, Chet C.,Yone, Nang S.,Gallin, Connor F.,Byers, Jeffery A.
, p. 14661 - 14664 (2020/12/02)
The first stereoconvergent Suzuki-Miyaura cross-coupling reaction was developed to afford enantioenriched 1,1-diarylalkanes. An iron-based complex containing a chiral cyanobis(oxazoline) ligand framework was best to obtain enantioenriched 1,1-diarylalkanes from cross-coupling reactions between unactivated aryl boronic esters and benzylic chlorides. Enhanced yields were obtained when 1,3,5-trimethoxybenzene was used as an additive, which is hypothesized to extend the lifetime of the iron-based catalyst. Exceptional enantioselectivities were obtained with challenging ortho-substituted benzylic chlorides. This journal is
Palladium-catalyzed regioselective hydroboration of aryl alkenes with B2pin2
Huang, Jiuzhong,Yan, Wuxin,Tan, Chaowei,Wu, Wanqing,Jiang, Huanfeng
, p. 1770 - 1773 (2018/02/21)
A palladium(ii)-catalyzed hydroboration of aryl alkenes with stable and easy-to-handle (pinacolato)diboron (B2pin2) under mild conditions has been developed. Acetic acid acted as the solvent and the hydrogen source, which has been identified by deuterium experiments. Notably, isomerization-hydroboration of allyl benzene derivatives was observed. As a result, a series of benzyl boronic esters were obtained in moderate to excellent yields with exclusive regioselectivity.
One-pot reductive coupling reactions of acetyl naphthalene derivatives, tosylhydrazide, with arylboronic acids
Shen, Xu,Liu, Ping,Liu, Yang,Liu, Yan,Dai, Bin
supporting information, p. 785 - 793 (2017/01/16)
In this study, a one-pot two-step reductive coupling between acetyl naphthalene derivatives, tosylhydrazide, and arylboronic acids, affording substituted 1(or 2)-(1-phenylethyl)naphthalenes in moderate-to-excellent yields, was reported. Notably, solvent played a crucial role in the coupling of 1-acetyl naphthalene derivatives (toluene) or 2-acetyl naphthalene derivatives (1,4-dioxane) as starting materials. Meanwhile, the scope of this one-pot coupling reaction was extended to 1(or 2)-naphthaldehyde substrates. Particularly, the system was also suitable to synthesize 1(or 2)-(1-phenylethyl)naphthalenes on a multi-gram scale, and was applied in the synthesis of naphthylmethyl substituted carbazolyl compounds.
Practical Cross-Coupling between O-Based Electrophiles and Aryl Bromides via Ni Catalysis
Cao, Zhi-Chao,Luo, Qin-Yu,Shi, Zhang-Jie
supporting information, p. 5978 - 5981 (2016/12/09)
Cross-coupling of various O-based electrophiles with aryl bromides was developed through Ni-catalyzed C-O activation in the presence of magnesium. Beside carboxylates, carbamates, and ethers, phenols exhibited excellent reactivity under modified conditions. This chemistry was featured as a simple and environmentally benign process with low catalyst loading and easy manipulations. The method exhibited broad substrate scopes.
1,3-dicyclohexylimidazol-2-ylidene as a superior ligand for the nickel-catalyzed cross-couplings of aryl and benzyl methyl ethers with organoboron reagents
Tobisu, Mamoru,Yasutome, Ayaka,Kinuta, Hirotaka,Nakamura, Keisuke,Chatani, Naoto
supporting information, p. 5572 - 5575 (2015/02/19)
A new catalytic system has been developed involving the use of Ni(cod)2 in conjunction with 1,3-dicyclohexylimidazol-2-ylidene for the cross-coupling of aryl and benzyl methyl ethers with organoboron reagents. This method not only allows for the use of readily available methyl ethers as halide surrogates but also provides a functional group tolerant method for the late-stage derivatization of complex molecules.
Superacid BF3-H2O promoted benzylation of arenes with benzyl alcohols and acetates initiated by trace water
Zhang, Shuting,Zhang, Xiaohui,Ling, Xuege,He, Chao,Huang, Ruofeng,Pan, Jing,Li, Jiaqiang,Xiong, Yan
, p. 30768 - 30774 (2014/08/05)
A convenient procedure employing simple starting materials benzyl alcohols and acetates as the benzyl donors to assemble a series of diarylalkanes through benzylation of arenes using in situ prepared superacid BF3-H 2O as an efficient promoter has been developed. The beneficial role of water in the reaction has been clarified with combination of control experiments and 11B NMR analysis. This reaction is a self-promoted model, which is triggered by the trace of water and continuously promoted by self released by-product water (or carboxylic acid). A wide range of substrates are investigated and the moderate to excellent yields and the good regioselectivities for secondary benzyl alcohols as well as arenes bearing electron-withdrawing groups have been achieved. As a result, moisture in the reaction system has been utilized as an efficient initiator in all benzylation cases.
The addition of simple aromatic hydrocarbons to condensed aromatic thiophenes promoted by aluminum chloride. Part II. Naphthothiophene
Clark, Peter David,McKinnon, David M.
, p. 1297 - 1302 (2007/10/02)
The reaction of naphthothiophene with an aromatic hydrocarbon in the presence of aluminum chloride at 20 deg C gave either a 3-aryl-2,3-dihydronaphthothiophene by addition to the 2,3-bond or 2,3-dihydronaphthothiophene as a result of hydride abstraction.Occasionally 2-aryl-2,3-dihydronaphthothiophenes were obtained.At higher temperatures 2-arylnaphthothiophenes and 2,3-dihydronaphthothiophene were isolated.Attempts are made to rationalize the formation of these products in terms of protonation of naphthothiophene by moist aluminum chloride and reaction of the resulting electrophile with an aromatic substrate.
