18019-57-3Relevant academic research and scientific papers
Palladium-Catalyzed Regioselective Acylation of Diazines with Toluenes: A New Approach to the Synthesis of ortho-Diacylbenzenes
Afaridoun, Hadi,Kianmehr, Ebrahim,Seifinoferest, Behnoush
, (2020/08/13)
A highly efficient and practical procedure for chemo- and regioselective synthesis of ortho-diacylbenzenes through Pd-catalyzed oxidative C–H bond activation has been developed. Using this method, a variety of ortho-diacylbenzenes were prepared in moderate to good yields, by direct acylation of diazines with toluene derivatives as acylation source. Ortho-diacylbenzenes may be used as precursors in synthesis of pharmaceuticals and agrochemicals.
Iodine-Mediated Cyclization of ortho-Alkynylaryl Ketones for the Synthesis of Indenone Derivatives
Chuangsoongnern, Pennapa,Surinrach, Chareef,Tummatorn, Jumreang,Thongsornkleeb, Charnsak,Ruchirawat, Somsak
, p. 5102 - 5109 (2017/09/23)
A new method for the synthesis of indenone derivatives based on the I2-promoted cyclization of ortho-alkynylaryl ketones has been developed. This method provides a metal-free and convenient route for the regioselective synthesis of indenones using ortho-alkynylaryl ketones with predefined substituents to give indenone products in moderate to good yields.
Pd(II)-Catalyzed Direct ortho-C-H Acylation of Aromatic Ketones by Oxidative Decarboxylation of α-Oxocarboxylic Acids
Lee, Pui-Yiu,Liang, Peiwen,Yu, Wing-Yiu
supporting information, p. 2082 - 2085 (2017/04/28)
A Pd-catalyzed decarboxylative acylation of aromatic ketones with α-oxocarboxylic acids was developed, and 1,2-diacylbenzenes were formed in up to 90% yield with excellent ortho-selectivity. This work demonstrates the first successful attempt to direct C-H acylation of aromatic ketones without the need for prederivatization to imines. The acylation reaction was inhibited by radical scavengers such as TEMPO, and 2,2,6,6-tetramethylpiperidin-1-yl benzoate, the adduct of TEMPO and a benzoyl radical, has been isolated and characterized. This finding is compatible with the intermediacy of acyl radicals. A mechanism involving the reaction of the palladacyclic complexes of aryl ketones with acyl radicals is proposed.
NHPI and palladium cocatalyzed aerobic oxidative acylation of arenes through a radical process
Liang, Yu-Feng,Wang, Xiaoyang,Tang, Conghui,Shen, Tao,Liu, Jianzhong,Jiao, Ning
, p. 1416 - 1419 (2016/01/25)
The NHPI and palladium cocatalyzed radical oxidative acylation of arenes with aldehydes and alcohols as acyl equivalents via selective C-H functionalization has been described. Molecular oxygen, the most environmentally friendly oxidant, was used as the terminal oxidant in this catalytic cycle.
Regioselective quadruple domino aldolization/aldol condensation/Michael/ SNAr-cyclization: Construction of hexacyclic indeno-fused C-nor-D-homo-steroid frameworks
Chanda, Tanmoy,Chowdhury, Sushobhan,Ramulu, B. Janaki,Koley, Suvajit,Jones, Raymond C.F.,Singh, Maya Shankar
supporting information, p. 2190 - 2194 (2014/03/21)
An operationally simple and highly atom-economic anionic quadruple domino reaction sequence for the synthesis of hexacyclic indeno-fused naphthalene/quinoline molecules having structural resemblance with the C-nor-D-homo-steroid nucleus has been developed. Promoter and solvent specificity, regioselectivity and mechanistic details were experimentally established. Catalyst concentration and solvent dependent switching of domino steps creating four new C-C bonds are discussed.
Iodine-promoted oxidative conversion of o-vinyl diaryl ketones into o-acetyl diaryl ketones, synthesis of 1-methyl-4-arylphthalazines as analogues of podophyllotoxin
Harikrishna, Kommidi,Mukkamala, Ramesh,Hinkelmann, Bettina,Sasse, Florenz,Aidhen, Indrapal Singh
, p. 1066 - 1075 (2014/03/21)
A new method is described for the metal-free oxidation of o-vinyl diaryl ketones in the presence of molecular iodine or N-iodosuccinimide to give o-acetyl diaryl ketones. This transformation involves the initial formation of an iodohydrin, and the o-carbo
Iodine-promoted oxidative conversion of o-vinyl diaryl ketones into o-acetyl diaryl ketones, synthesis of 1-methyl-4-arylphthalazines as analogues of podophyllotoxin
Harikrishna, Kommidi,Mukkamala, Ramesh,Hinkelmann, Bettina,Sasse, Florenz,Aidhen, Indrapal Singh
, p. 1066 - 1075 (2015/10/05)
A new method is described for the metal-free oxidation of o-vinyl diaryl ketones in the presence of molecular iodine or N-iodosuccinimide to give o-acetyl diaryl ketones. This transformation involves the initial formation of an iodohydrin, and the o-carbo
Pd(ii)-catalyzed direct C-H acylation of N-Boc hydrazones with aldehydes: One-pot synthesis of 1,2-diacylbenzenes
Sharma, Satyasheel,Kim, Aejin,Park, Jihye,Kim, Mirim,Kwak, Jong Hwan,Jung, Young Hoon,Park, Jung Su,Kim, In Su
, p. 7869 - 7876 (2013/11/19)
A palladium(ii)-catalyzed direct acylation of acetophenone N-Boc hydrazones with aldehydes via C-H bond activation is described. This protocol provides direct access to a range of 1,2-diacylbenzenes, which are useful precursors to construct biologically interesting and pharmaceutically important compounds.
Rhodium-catalyzed oxidative ortho-acylation of aryl ketone O-methyl oximes with aryl and alkyl aldehydes
Yang, Yaxi,Zhou, Bing,Li, Yuanchao
, p. 2916 - 2920 (2013/01/15)
The rhodium-catalyzed oxidative ortho-acylation of aryl ketone O-methyl oximes with aryl and alkyl aldehydes via C-H bond activation is described. The cross-coupling reaction exhibits high functional group tolerance and regioselectivity under relatively m
Synthesis of bisisoindolomethene dyes bearing anisole or ethylthiophene residues for red and near-IR fluorescence
Ulrich, Gilles,Goeb, Sébastien,De Nicola, Antoinette,Retailleau, Pascal,Ziessel, Raymond
, p. 1517 - 1520 (2008/02/05)
New difluorobora-diisoindolomethenes dyes were synthesized from carbohydrazide and o-hydroxy-acetophenone derivatives bearing phenyl, p-anisole or ethylthiophene substituents. The nature of the substituents allows modulating the fluorescence from 650 nm t
