948-55-0Relevant academic research and scientific papers
Electrochemical fluorosulfonylation of alkenes to access vicinal fluorinated sulfones derivatives
Zhao, Bin,Pan, Zichen,Zhu, Anqiao,Yue, Yanni,Ma, Mengtao,Xue, Fei
supporting information, (2022/01/24)
Herein, we report a practical and efficient fluorosulfonylation of the various alkenes with sulfonyl radical sources (RSO2NHNH2) and Et3N·3HF as cost-effective fluorination reagents under mild conditions. Remarkably, this
Photoredox-Catalyzed α-Aminomethyl Carboxylation of Styrenes with Sodium Glycinates: Synthesis of γ-Amino Acids and γ-Lactams
Zhou, Cong,Li, Miao,Sun, Jianwei,Cheng, Jiang,Sun, Song
supporting information, p. 2895 - 2899 (2021/05/05)
A visible-light photoredox-catalyzed reductive α-aminomethyl carboxylation of styrenes with sodium glycinates and CO2 has been developed to synthesize a series of α,α-disubstituted γ-amino acids and γ-lactams with high efficiency and regioselectivity. Notably, CO2 released from the decarboxylation step can be reused for the subsequent carboxylation. Distinct from the previous reactions with the same type of substrates leading to simple decarboxylation and olefin hydroalkylation, this process involves additional CO2 sequestration, thus leading to olefin α-aminomethyl carboxylation. These findings not only provide new access to α,α-disubstituted γ-amino acids and γ-lactams but also serve as a proof of concept for CO2 reutilization in decarboxylation reactions.
Pd/GF-Phos-Catalyzed Asymmetric Three-Component Coupling Reaction to Access Chiral Diarylmethyl Alkynes
Zhao, Guofeng,Wu, Yi,Wu, Hai-Hong,Yang, Junfeng,Zhang, Junliang
supporting information, p. 17983 - 17988 (2021/11/16)
Significant attention has been given in the past few years to the selective transformations of N-tosylhydrazones to various useful compounds. However, the development of enantioselective versions poses considerable challenges. Herein we report a Pd-catalyzed enantioselective three-component coupling of N-tosylhydrazone, aryl halide, and terminal alkyne under mild conditions utilizing a novel chiral sulfinamide phosphine ligand (GF-Phos), which provides a facile access to chiral diarylmethyl alkynes, which are useful synthons in organic synthesis as well as exist as the skeleton in many bioactive molecules. A pair of enantiomers of the product could be easily prepared using the same chiral ligand by simply changing the aryl substituents of the N-tosylhydrazone and aryl halide. The salient features of this reaction include the readily available starting materials, general substrate scope, high enantioselectivity, ease of scale-up, mild reaction conditions, and versatile transformations.
Photoinduced Hydroarylation and Cyclization of Alkenes with Luminescent Platinum(II) Complexes
Cheng, Hanchao,Lam, Tsz-Lung,Liu, Yungen,Tang, Zhou,Che, Chi-Ming
supporting information, p. 1383 - 1389 (2020/11/30)
Photoinduced hydroarylation of alkenes is an appealing synthetic strategy for arene functionalization. Herein, we demonstrated that aryl radicals generated from electron-deficient aryl chlorides/bromides could be trapped by an array of terminal/internal aryl alkenes in the presence of [Pt(O^N^C^N)] under visible-light (410 nm) irradiation, affording anti-Markovnikov hydroarylated compounds in up to 95 % yield. Besides, a protocol for [Pt(O^N^C^N)]-catalyzed intramolecular photocyclization of acrylanilides to give structurally diverse 3,4-dihydroquinolinones has been developed.
Visible-Light-Induced Meerwein Fluoroarylation of Styrenes
Tang, Hai-Jun,Zhang, Bin,Xue, Fei,Feng, Chao
supporting information, p. 4040 - 4044 (2021/05/26)
An unprecedented approach for assembling a broad range of 1,2-diarylethane derivatives with fluorine-containing fully substituted carbon centers was developed. The protocol features straightforward operation, proceeds under metal-free condition, and accommodates a large variety of synthetically useful functionalities. The critical aspect to the success of this novel transformation lies in using aryldiazonium salts as both aryl radical progenitor and also as single electron acceptor which elegantly enables a radical-polar crossover manifold.
TMSOTf-mediated synthesis of skipped dienes through the addition of olefins to imines and semicyclicN,O-acetals
Feng, Yi-Man,Nie, Xiao-Di,Sun, Jian-Ting,Wei, Bang-Guo,Xu, Wen-Ke
, p. 7883 - 7893 (2021/09/28)
A novel approach to skipped dienes has been developed through the TMSOTf-mediated one-pot addition-substitution of olefins2a,2fand2gwith imines1a-1g, and a series of aryl substituted skipped dienes3aa-3gfwere accordingly obtained in 62%-94% yields. Moreov
A mechanistic investigation of the Pd-catalyzed cross-coupling between: N -tosylhydrazones and aryl halides
Mcindoe, J. Scott,Ronda, Kiera,Thomas, Gilian T.
supporting information, p. 15533 - 15537 (2021/12/02)
The cross-coupling of N-tosylhydrazones and aryl halides forms carbon-carbon bonds, producing 1,1-disubstituted alkenes. Though it has proven extremely useful in several fields of chemistry, its mechanism remains experimentally unexplored. Combining benchtop NMR and real-time mass spectrometry afforded the ability to monitor the catalytic intermediates as well as the rate of product formation. This journal is
Deaminative carbonylative coupling of alkylamines with styrenes under transition-metal-free conditions
Zhao, Fengqian,Li, Chong-Liang,Wu, Xiao-Feng
supporting information, p. 9182 - 9185 (2020/08/26)
A transition-metal-free deaminative carbonylation of alkylamines with styrenes has been developed. The reaction shows good functional group compatibility and various α,β-unsaturated ketones were obtained in moderate to good yields. The alkyl radical generated from Katritzky salts via base-promoted C-N bond cleavage is one of the key intermediates in this reaction. This journal is
Direct suzuki-miyaura coupling with naphthalene-1,8-diaminato (dan)-substituted organoborons
Yoshida, Hiroto,Seki, Michinari,Kamio, Shintaro,Tanaka, Hideya,Izumi, Yuki,Li, Jialun,Osaka, Itaru,Abe, Manabu,Andoh, Hiroki,Yajima, Tomoki,Tani, Tomohiro,Tsuchimoto, Teruhisa
, p. 346 - 351 (2019/12/24)
The actually direct Suzuki-Miyaura coupling with "protected" R-B(dan) (dan = naphthalene-1,8-diaminato) was demonstrated to smoothly occur without in situ deprotection of the B(dan) moiety. The use of t-BuOK (Ba(OH)2 in some cases) as a base under anhydrous conditions is the key to the successful cross-coupling, where R-B(dan) is readily converted into a transmetalation-active borate-form, regardless of the well-accepted diminished boron-Lewis acidity.
Cu/Ni-Catalyzed Cyanomethylation of Alkenes with Acetonitrile for the Synthesis of β,γ-Unsaturated Nitriles
Jian, Hong,Shen, Zengming,Zhang, Saisai
, p. 6143 - 6150 (2020/05/22)
We have developed a protocol for the Cu/Ni-catalyzed cyanomethylation of alkenes with acetonitrile for the synthesis of β,γ-unsaturated nitriles. This is the first example of a direct coupling of the alkene sp2 C - H bond and the acetonitrile sp3 C - H bond for the preparation of β,γ-unsaturated nitriles. Acetonitrile, an inexpensive and stable solvent, is demonstrated to be a useful cyanomethyl source. The combination of copper and nickel catalysts resulted in a high reaction efficiency.
