1283668-80-3Relevant academic research and scientific papers
Completely Stereoselective Synthesis of Sulfonated 1,3-Dihydroisobenzofurans via Radical Multicomponent Reactions
Shi, Hao-Nan,Huang, Min-Hua,He, Chun-Lan,Lu, Hai-Ping,Hao, Wen-Juan,Tu, Xing-Chao,Tu, Shu-Jiang,Jiang, Bo
, p. 13686 - 13695 (2019/10/16)
Two types of new oxidant-free radical multicomponent reactions of β-alkynyl ketones, aryldiazonium salts, and DABCO·(SO2)2 (DABSO) were established, leading to the tunable generation of two class of sulfonated 1,3-dihydroisobenzofurans with moderate to good yields and complete stereoselectivity under the mild conditions. The radical-induced scission/recombination of the C(sp3)-C(sp3) bond enabled direct 1,8-halosulfonylation of β-alkynyl ketones, giving 1,3-dimethylene-substituted (1Z,3Z)-1,3-dihydroisobenzofurans with substituent diversity by p-nitrobenzyl bromide (PNBB) or p-nitrobenzyl chloride (PNBC) as the halo source. Fine-tuning substituents to strong electron-withdrawing ones, such as nitro, cyano, and trifluoromethyl, linked to aryldiazonium tetrafluoroborates allowed a different annulation/1,5-azosulfonylation process to access sulfonated (Z)-1,3-dihydroisobenzofurans with one quaternary carbon-amino functionality.
Stereospecific Synthesis of (Z,Z)-Isobenzofurans via Radical-Enabled Cleavage of C(sp3)?C(sp3) and C(sp2)-Halogen Bonds
Huang, Min-Hua,Shi, Hao-Nan,Zhu, Chi-Fan,He, Chun-Lan,Hao, Wen-Juan,Tu, Shu-Jiang,Jiang, Bo
supporting information, p. 5340 - 5345 (2019/11/14)
A novel radical-induced annulation/1,8-halosulfonylation of β-alkynyl ketones with haloaryl diazonium tetrafluoroborates and DABCO.bis(sulfur dioxide) was first achieved via the cleavage/recombination of C(sp3)?C(sp3) and C(sp2)-halogen bonds, from which 47 examples of sulfone-containing 1,3-dimethylene-substituted (Z,Z)-isobenzofurans as single stereoisomers were synthesized in generally good yields. This multicomponent pathway is proposed to proceed through the in-situ generation of arylsulfonyl radicals, followed by selective radical addition-cyclization and ring-opening of the cyclopropyl unit as well as C(sp2)-halogen bond cleavage, resulting in the consecutive construction of three new chemical bonds, including C?S, C?O and C-halogen bonds. (Figure presented.).
A gold-catalyzed cycloisomerization/aerobic oxidation cascade strategy for 2-aryl indenones from 1,5-enynes
Guo, Jia,Peng, Xiaoshi,Wang, Xiaoyu,Xie, Fukai,Zhang, Xinhang,Liang, Guoduan,Sun, Zenghui,Liu, Yongxiang,Cheng, Maosheng,Liu, Yang
supporting information, p. 9147 - 9151 (2019/01/03)
A unique gold(i)-catalyzed 5-endo-dig cyclization/aerobic oxidation cascade strategy from 1,5-enyne substrates with molecular oxygen as the oxidant to yield the indenone was described. The reaction mechanism was studied by heavy atom labelling and some related experiments. This method was applied to the formal total synthesis of isoprekinamycin.
Au(i)-catalyzed triple bond alkoxylation/dienolether aromaticity-driven cascade cyclization to naphthalenes
Liu, Yongxiang,Guo, Jia,Liu, Yang,Wang, Xiaoyu,Wang, Yanshi,Jia, Xinyu,Wei, Gaofei,Chen, Lizhu,Xiao, Jianyong,Cheng, Maosheng
supporting information, p. 6243 - 6245 (2014/06/09)
A novel strategy for the synthesis of multisubstituted naphthalenes was developed via a Au(i)-catalyzed alkyne alkoxylation/dienolether aromaticity-driven cascade cyclization using 1,5-enyne substrates. The functional group toleration was examined by synthesizing a series of substrates and the mechanism was also studied based on intermediates isolated through deuterium labeling experiments. This journal is the Partner Organisations 2014.
NHC-catalyzed oxidative cyclization reactions of 2-alkynylbenzaldehydes under aerobic conditions: Synthesis of O-Heterocycles
Park, Jong Hyub,Bhilare, Sachin V.,Youn, So Won
, p. 2228 - 2231 (2011/07/09)
Chemical equations presented. An NHC-catalyzed, regio- and stereoselective oxidative cyclization of o-alkynylbenzaldehydes bearing an unactivated alkyne moiety as an internal electrophile has been developed to afford phthalides and isocoumarins. A single organocatalytic system enabled two sequential C-O bond formations to take place in an atom economical manner via highly efficient dual activation. Molecular oxygen in air could be utilized as a source of an oxygen atom for the oxidation of aldehydes to the corresponding benzoic acids under our newly developed reagent system.
