3117-37-1Relevant academic research and scientific papers
Nickel-Catalyzed Decarbonyloxidation of 3-Aryl Benzofuran-2(3H)-ones to 2-Hydroxybenzophenones
Tong, Zhou,Tang, Zhi,Au, Chak-Tong,Qiu, Renhua
, p. 8533 - 8543 (2020/07/16)
We have developed a protocol to facilitate the nickel-catalyzed decarbonyloxidation of 3-aryl benzofuran-2(3H)-ones to 2-hydroxybenzophenones under mild conditions, which is an efficient approach for the decarbonyloxidation of lactones in organic synthesis. A diverse range of substrates can undergo C(O)-O/C(O)-C bond cleavage to generate the target products in good yields. These 2-hydroxybenzophenones can be converted into a variety of compounds via reactions such as esterification, cyclization, and reduction.
A benzofuran compound and its efficient catalytic synthesis method
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Paragraph 0019; 0020, (2019/04/04)
The invention discloses a to trifluoromethanesulfonic acid nickel as catalyst, in order to mandelic acid and phenol as raw materials, and efficient synthesis of the benzofuran compound of the method, this method has the advantages of low cost, high yield,
Recyclable nickel-catalyzed C-H/O-H dual functionalization of phenols with mandelic acids for the synthesis of 3-aryl benzofuran-2(3: H)-ones under solvent-free conditions
Tang, Zhi,Tong, Zhou,Xu, Zhihui,Au, Chak-Tong,Qiu, Renhua,Yin, Shuang-Feng
supporting information, p. 2015 - 2022 (2019/04/27)
Herein, we developed a protocol for the efficient synthesis of 3-aryl benzofuran-2(3H)-ones under solvent-free conditions from phenols and mandelic acids using Ni(OTf)2 as a catalyst. A diverse range of mandelic acids and phenols undergo C-H/O-
Strategy for Catalytic Chemoselective Cross-Enolate Coupling Reaction via a Transient Homocoupling Dimer
Tanaka, Takafumi,Tanaka, Tsukushi,Tsuji, Taro,Yazaki, Ryo,Ohshima, Takashi
supporting information, p. 3541 - 3544 (2018/06/26)
A new strategy, a transient homocoupling dimer strategy, for direct catalytic oxidative cross-enolate coupling reactions is developed. Cross-enolate coupling products bearing a (contiguous) tetrasubstituted carbon center were obtained chemoselectively without the need for stoichiometric amounts of strong bases/metal oxidants, and thus, the present catalysis provides a general method for the synthesis of unnatural α,α-disubstituted amino acid motifs. The distinct transformation of azlactone and 2-acylimidazole units highlighted the synthetic utility of the present catalysis.
Phosphine-Catalyzed Domino β/γ-Additions of Benzofuranones with Allenoates: A Method for Unsymmetrical 3,3-Disubstituted Benzofuranones
Huang, Zhusheng,Yang, Xiuqin,Yang, Fulai,Lu, Tao,Zhou, Qingfa
supporting information, p. 3524 - 3527 (2017/07/17)
A phosphine-catalyzed domino process of benzofuranones with allenoates has been developed which furnishes highly functionalized unsymmetrical 3,3-disubstituted benzofuranones in synthetically useful yields. The mechanism for the transformation is a tandem β-umpolung/γ-umpolung process.
Direct enantioselective: C -acylation for the construction of a quaternary stereocenter catalyzed by a chiral bicyclic imidazole
Wang, Mo,Zhang, Xiao,Ling, Zheng,Zhang, Zhenfeng,Zhang, Wanbin
supporting information, p. 1381 - 1384 (2017/02/05)
A direct enantioselective C-acylation of 3-substituted benzofuran-2(3H)-ones (with up to 97% ee) was developed using a chiral bicyclic imidazole catalyst OAc-DPI and an achiral tertiary amine additive DIPEA. The reaction mechanism for the direct C-acylation has been investigated using both experimental and theoretical studies.
SbCl3-catalyzed solvent-free Friedel–Crafts reaction of phenols with mandelic acids to 3-aryl benzofuran-2(3H)-ones: Synthesis of spirocyclic 2,3-dihydrobenzofuran-2-ones
Dhotare, Bhaskar B.,Choudhary, Manoj K.,Nayak, Sandip K.
supporting information, p. 1772 - 1780 (2016/10/31)
A facile, SbCl3-catalyzed, one-pot, tandem Friedel–Crafts/lactonization reaction of phenols and mandelic acids has been developed under solvent-free conditions to afford 3-aryl benzofuran-2(3H)-ones in good to high yields (52–90%). Additionally
(C6F5)3B Catalyzed Chemoselective and ortho-Selective Substitution of Phenols with α-Aryl α-Diazoesters
Yu, Zhunzhun,Li, Yongfeng,Shi, Jiameng,Ma, Ben,Liu, Lu,Zhang, Junliang
, p. 14807 - 14811 (2016/11/23)
The development of an efficient method for the site-selective substitution of unprotected phenols has long been considered as an attractive but challenging task. Herein, we describe a highly chemo- and ortho-selective substitution reaction of phenols with α-aryl α-diazoacetates with commercially available (C6F5)3B as the catalyst. This reaction proceeds under simple and mild conditions with high efficiency, it features a wide substrate scope and can be easily scaled up.
A Concise Synthesis of 2-(2-Hydroxyphenyl)acetonitriles via the o-Quinone Methides Generated from 2-(1-Tosylalkyl)phenols
Wu, Bo,Gao, Xiang,Chen, Mu-Wang,Zhou, Yong-Gui
, p. 981 - 984 (2016/02/18)
A concise synthesis of 2-(2-hydroxyphenyl)acetonitriles has been developed through reaction of trimethylsilyl cyanide and the o-quinone methides in situ generated from 2-(1-tosylalkyl)phenols under basic conditions. In addition, 2-(2-hydroxyphenyl)acetonitriles could be conveniently transformed to benzofuranones.
Chemistry of photogenerated α-phenyl-substituted o-, m-, and p-quinone methides from phenol derivatives in aqueous solution
Diao, Li,Wan, Peter
, p. 105 - 118 (2008/09/18)
The enhanced photochemical reactivity of o-substituted phenols in its propensity to give o-quinone methide (o-QM) intermediates via excited state intramolecular proton transfer (ESIPT) was uncovered by Keith Yates as part of his now classic studies of photohydration of aromatic alkenes, alkynes, and related compounds. Photogeneration of QMs and the study of their chemistry along with potential biological applications are the focus of many groups. In this work, photochemical precursors to o-, m-, and p-QMs based on substituted phenols (hydroxybenzyl alcohols) and related compounds have been studied in aqueous solution as a function of pH and water content. The focus will be on QMs that are stabilized by an a-phenyl substituent, which enhances quantum yields for their formation, with the resulting QMs having longer lifetimes and easier to detect. Noteworthy is that all QM isomers can. be photogenerated with the o and m isomers being the most efficient, consistent with the Zimmerman "ortho-meta" effect. m-QMs have formal non-Kekule structures, and although they can be routinely photogenerated, are found to be most reactive. One m-QM was found, to undergo a photocondensation reaction at high pH giving rise to m-substituted oligomers. The mechanism, of QM formation in aqueous solution is believed to involve singlet excited phenols that undergo adiabatic deprotonation to give the corresponding photoexcited phenolate ion, which subsequently expels the hydroxide ion (photodehydroxylation). A pathway involving direct loss of water for the o-isomers is also possible in organic solvents.
