184368-89-6Relevant articles and documents
Hydroxyl Assisted, Photoredox/Cobalt Co-catalyzed Semi-Hydrogenation and Tandem Cyclization of o-Alkynylphenols for Access to 2,3-Dihydrobenzofurans
Tian, Wan-Fa,Zhu, Yao,He, Yong-Qin,Wang, Mei,Song, Xian-Rong,Bai, Jiang,Xiao, Qiang
supporting information, p. 730 - 736 (2020/12/15)
Herein, a hydroxyl assisted, photoredox/cobalt co-catalyzed semi-hydrogenation and tandem cyclization of o-alkynylphenols is developed towards direct assembly of 2,3-dihydrobenzofurans. Moderate to good yields were obtained for a range of sterically and electronically diverse 2-propynolphenols under mild conditions. Mechanistic studies demonstrated the inevitable role of the alcoholic hydroxyl group with (Z)-alkene as the real intermediate. Finally, a key low-valent cobalt catalyzed intramolecular hydroetherification of alkene is proposed. (Figure presented.).
Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions
Costello, Jeff P.,Ferreira, Eric M.
supporting information, p. 9934 - 9939 (2019/12/24)
The steric and electronic drivers of regioselectivity in platinum-catalyzed intramolecular hydroalkoxylation are elucidated. A branch point is found that divides the process between 5-exo and 6-endo selective processes, and enol ethers can be accessed in good yields for both oxygen heterocycles. The main influence arises from an electronic effect, where the alkyne substituent induces a polarization of the alkyne that leads to preferential heteroatom attack at the more electron-deficient carbon. The electronic effects are studied in other contexts, including hydroacyloxylation and hydroamination, and similar trends in directionality are predominant although not uniformly observed.
Catalytic Synthesis of Trifluoromethylated Allenes, Indenes, Chromenes, and Olefins from Propargylic Alcohols in HFIP
No?l, Florent,Vukovi?, Vuk D.,Yi, Jing,Richmond, Edward,Kravljanac, Pavle,Moran, Joseph
, p. 15926 - 15947 (2019/12/25)
A general method to access CF3-substituted allenes from propargylic alcohols under Lewis acid catalysis in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as solvent is described. By tuning the reaction time and temperature, the obtained allenes rearr
Synthesis and evaluation of (E)-2-(5-phenylpent-2-en-4-ynamido)cyclohex-1-ene-1-carboxylate derivatives as HCA2 receptor agonists
Bobileva, Olga,Ikaunieks, Martins,Duburs, Gunars,Mandrika, Ilona,Petrovska, Ramona,Klovins, Janis,Loza, Einars
, p. 4314 - 4329 (2017/07/22)
Novel series of compounds consisting of 2-amidocyclohex-1-ene carboxylate and phenyl parts which are connected by enyne (compounds 2a–f), but-1-yne (compounds 4a–j), and phenylethylene (compounds 5a–f) linkers as HCA2 full agonists were designed and their
Csp2-Csp2 and Csp2-N Bond Formation in a One-Pot Reaction between N-Tosylhydrazones and Bromonitrobenzenes: An Unexpected Cyclization to Substituted Indole Derivatives
Bzeih, Tourin,Lamaa, Diana,Frison, Gilles,Hachem, Ali,Jaber, Nada,Bignon, Jerome,Retailleau, Pascal,Alami, Mouad,Hamze, Abdallah
supporting information, p. 6700 - 6703 (2017/12/26)
A novel, sequential, palladium-catalyzed, cross-coupling reaction using N-tosylhydrazone and bromonitrobenzene derivatives followed by reductive cyclization has been developed. This transformation providing an efficient route to unexpected N-arylindole derivatives involves, in a one-pot reaction, the formation of one Csp2-Csp2 bond and two Csp2-N bonds together with the cleavage of one Csp2-heteroatom bond. Evaluation of the biological activity led to the identification of compound 5a, which displays potent activity at nanomolar concentrations against human colon carcinoma cell line.
Gold-Catalyzed Fluorination–Hydration: Synthesis of α-Fluorobenzofuranones from 2-Alkynylphenol Derivatives
Wang, Qiang,Jiang, Yu,Sun, Run,Tang, Xiang-Ying,Shi, Min
supporting information, p. 14739 - 14745 (2016/10/03)
The AuI-catalyzed fluorination–hydration of 2-alkynylphenol derivatives in the presence of Selectfluor [1-chloromethyl-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate)] has been developed. This method provides straightforward a
Gold(I)-Catalyzed Domino Cyclization for the Synthesis of Tricyclic Chromones
Li, Zhiqiang,Li, Qingjiang,Liu, Guo-Kai,Chen, Weimin,Peng, Xiao-Shui,Wong, Henry N. C.
supporting information, p. 1461 - 1464 (2015/06/30)
A simple and efficient method for the synthesis of tricyclic chromones has been developed. In this approach, tricyclic chromones were synthesized from a diverse range of phenols and alkynes through a Sonogashira coupling and subsequent gold-catalyzed intr
Rhodium(III)-catalyzed direct C-2 olefination of unactivated indoles utilizing OH/NH2 as directing group
Tang, Chen-Yu,Tao, Yuan,Wu, Xin-Yan,Sha, Feng
supporting information, p. 609 - 615 (2014/05/20)
Oxidative C-2 olefination of indoles/pyrrole via rhodium(III)-catalyzed direct C-H bond activation is reported. Phenolic OH and aniline NH2 units were revealed to be effective chelating groups to activate the aryl C-H bond. The reactions proceeded with ex
One-pot synthesis of 2,2′-bisbenzofurans using cuprous chloride as a catalyst
Pan, Wen-Bin,Chen, Chin-Chau,Wei, Li-Lan,Wei, Li-Mei,Wu, Ming-Jung
, p. 2655 - 2657 (2013/06/05)
A variety of novel 5,5′-disubstituted-2,2′-bisbenzofuran derivatives were synthesized by treatment of 4-substituted-2-(2- trimethylsilylethynyl)phenyl tert-butyldimethylsilyl ether analogues with CuCl as a catalyst in 62-82% isolated yields. This novel st
A route to 5-substituted dibenzofurans by anionic cycloaromatization of 2-(6-substituted 3-hexen-1,5-diynyl)phenyl tert-butyldimethyl ethers and related molecules
Wu, Ming-Jung,Lee, Chia-Ying,Lin, Chi-Fong
, p. 4077 - 4079 (2007/10/03)
An anionic cycloaromatization reaction provides an efficient method for the synthesis of the dibenzofurans 2 by treatment of the tert-butyldimethylsilyl ethers 1 with sodium methoxide or potassium carbonate in methanol at reflux for 16 h, and gives 50-94%
