1580-52-5Relevant academic research and scientific papers
Access to Diarylmethanols by Wittig Rearrangement of ortho-, meta-, and para-Benzyloxy- N-Butylbenzamides
Aitken, R. Alan,Harper, Andrew D.,Inwood, Ryan A.,Slawin, Alexandra M. Z.
, p. 4692 - 4701 (2022/04/07)
The N-butyl amide group, CONHBu, has been found to be an effective promoter of the [1,2]-Wittig rearrangement of aryl benzyl ethers and thus allow the two-step synthesis of isomerically pure substituted diarylmethanols starting from simple hydroxybenzoic acid derivatives. The method is compatible with a wide range of functional groups including methyl, methoxy, and fluoro, although not with nitro and, unexpectedly, is applicable to meta as well as ortho and para isomeric series.
Direct and selective synthesis of 3-arylphthalides via nickel-catalyzed aryl addition/intramolecular esterification
Qiang, Qing,Liu, Feipeng,Rong, Zi-Qiang
supporting information, (2021/05/10)
Herein we report a nickel-catalyzed aryl addition/intramolecular esterification in a cascade fashion. Under the combination of commercially available nickel precursor and tridentate ligand, the one pot protocol offers a direct, simple and regioselective approach to access 3-aryl phthalide derivatives from two readily available substrates with good efficiency, broad scope as well as satisfactory functional group compatibility.
Cooperative iodine and photoredox catalysis for direct oxidative lactonization of carboxylic acids
Duhamel, Thomas,Mu?iz, Kilian
supporting information, p. 933 - 936 (2019/01/23)
A new method for the formation of γ- and δ-lactones from carboxylic acids through direct conversion of benzylic C-H to C-O bonds is described. The reaction is conveniently induced by visible light and relies on a mild cooperative catalysis by the combination of molecular iodine and an organic dye.
Rhenium-Catalyzed Phthalide Synthesis from Benzamides and Aldehydes via C-H Bond Activation
Jia, Bing,Yang, Yunhui,Jin, Xiqing,Mao, Guoliang,Wang, Congyang
, p. 6259 - 6263 (2019/09/06)
The [4 + 1] annulation of benzamides and aldehydes for phthalide synthesis was achieved via rhenium-catalyzed C-H activation, which demonstrates an unprecedented reaction pattern distinct from those of other transition-metal catalyses. The reaction also features readily available starting materials, a wide scope for both electro-rich and electro-deficient substrates, and the elimination of homoannulation byproducts.
Scalable Electrochemical Dehydrogenative Lactonization of C(sp2/sp3)-H Bonds
Zhang, Sheng,Li, Lijun,Wang, Huiqiao,Li, Qian,Liu, Wenmin,Xu, Kun,Zeng, Chengchu
supporting information, p. 252 - 255 (2018/01/17)
A practical, electrochemical method is developed for the direct dehydrogenative lactonization of C(sp2/sp3)-H bonds under external oxidant- and metal-free conditions, delivering diverse lactones, including coumarin derivatives with excellent regioselectivity. The scalable nature of this newly developed electrochemical process was demonstrated on a 40 g scale following an operationally simple protocol. The remote lactonization of C(sp3)-H bonds would constitute an important synthetic advance toward electrochemical C-O bond formation.
A One-pot preparation of 1,3-diarylisobenzofuran
Hamura, Toshiyuki,Nakayama, Ryosuke
supporting information, p. 1013 - 1015 (2013/09/24)
A simple, practical, and efficient method for one-pot synthesis of symmetric and unsymmetrical 1,3-diarylisobenzofurans has been developed by sequential reactions of methyl 2-formylbenzoate with two identical or different aryl metal species.
Rhodium or palladium-catalyzed cascade aryl addition/intramolecular lactonization of phthalaldehydonitrile to access 3-aryl and 3-alkenyl phthalides
Lv, Guanglei,Huang, Genping,Zhang, Guangyou,Pan, Changduo,Chen, Fan,Cheng, Jiang
supporting information; experimental part, p. 4879 - 4886 (2011/07/29)
A rhodium or palladium-catalyzed addition of boronic acids to phthalaldehydonitrile, followed by an intramolecular lactonization of cyano to access 3-substituted phthalides, is described. This procedure tolerates a series of functional groups, such as methoxy, fluoro, chloro, and vinyl groups. It is a novel procedure for the synthesis of 3-arylphthalides.
Rhodium or palladium-catalyzed cascade aryl addition/ intramolecular lactonization of phthalaldehyde with potassium organotrifluoroborates to access 3-arylphthalides
Luo, Fang,Pan, Shen,Pan, Changduo,Qian, Pengcheng,Cheng, Jiang
supporting information; experimental part, p. 320 - 324 (2011/04/23)
An efficient rhodium-catalyzed lactonization of phthalaldehyde with potassium organotrifluoroborates to access 3-arylphthalides has been developed. Moreover, palladium is a also good catalyst for such transformation.
Rhodium-catalyzed cascade reaction: Aryl addition/intramolecular esterification to access 3-aryl and 3-alkenyl phthalides
Ye, Zhishi,Lv, Guanglei,Wang, Wenhui,Zhang, Manli,Cheng, Jiang
supporting information; experimental part, p. 3671 - 3674 (2010/08/04)
Chemical Equation Reprentation First one and then the other: A rhodiumcatalyzed addition of aryl and alkenyl boronic acids to phthalaldehyde and subsequent intramolecular esterification is described (see scheme; cod = l,5-cyclooctadiene, dppb = 1,4-bis(diphenylphosphino)butane). The method is facile and practical for accessing 3-aryl and 3-alkenyl phthalides in moderate to good yields. Several functional groups are tolerated under the reaction conditions.
Palladium-catalyzed cascade aryl addition/intramolecular lactonization of phthalaldehyde to access 3-aryl- and alkenylphthalides
Ye, Zhishi,Qian, Pengcheng,Lv, Guanglei,Luo, Fang,Cheng, Jiang
supporting information; experimental part, p. 6043 - 6045 (2010/11/18)
A palladium-catalyzed addition of arylboronic acids to phthalaldehyde, followed by an intramolecular lactonization to access 3-substituted phthalides, is described. The procedure tolerates a series of functional groups, such as methoxyl, fluoro, chloro, and trifluoromethyl groups. It represents a procedure for the synthesis of 3-substituted phthalides.
