93877-37-3Relevant academic research and scientific papers
Metal-free [3 + 2 + 1] annulation of allylic alcohols, ketones, and ammonium acetate: radical-involving synthesis of 2,3-diarylpyridine derivatives
Ge, Danhua,Luo, Xin-Long,Tang, Xi,Pang, Chao-Bin,Wang, Xin,Chu, Xue-Qiang
supporting information, p. 2277 - 2283 (2021/03/24)
A three-component [3 + 2 + 1] annulation strategy for the synthesis of biologically and pharmaceutically active 2,3-diarylpyridine derivatives by using a series of allylic alcohols, ketones, and ammonium acetate as substrates has been developed. The method proceeds efficiently under metal-free conditions, and the desired heterocycles could be obtained in a site-specific selectivity manner with good functional group tolerance.
Photo-mediated [1, 3]-Carbonyl shift of β-Ketocarbonyls
Zhang, Wenzhao,Li, Yao,Luo, Sanzhong
, (2020/04/29)
An organic amine mediated photolytic [1,3]-benzoyl migration of β-benzoyl carbonyl compounds was reported. This migration was achieved by Norrish-Yang cyclization and retro-aldol reaction under black light (365 nm) or visible light irradiation. This photolytic protocol provides an alternative approach to the synthesis of 1,5-dicarbonyl compounds. By chiral primary amine catalysis, a kinetic resolution was also developed to afford enantioenriched 1,5-dicarbonyls.
Oxidative alkylation of alkenes with carbonyl compounds through concomitant 1,2-aryl migration by photoredox catalysis
Lin, Zhaowei,Lu, Maojian,Liu, Boyi,Gao, Jing,Huang, Mingqiang,Gan, Zhenhong,Cai, Shunyou
supporting information, p. 16031 - 16035 (2020/10/08)
Visible-light-enabled oxidative radical 1,2-alkylarylation of α-aryl allylic alcohols with carbonyl compounds has been established under mild conditions. An efficient and convenient protocol for the construction of a variety of 1,5-dicarbonyl compounds wa
Visible-light-induced 1,2-alkylarylation of alkenes with a-C(sp3)–H bonds of acetonitriles involving neophyl rearrangement under transition-metal-free conditions
Wang, Qiao-Lin,Chen, Zan,Zhou, Cong-Shan,Xiong, Bi-Quan,Zhang, Pan-Liang,Yang, Chang-An,Liu, Yu,Zhou, Quan
supporting information, p. 4551 - 4556 (2018/11/27)
An efficient visible-light-induced difunctionalization of alkenes with a-C(sp3)–H bonds of nitriles is described for the constructing of diverse 5-oxo-pentanenitriles under transition-metal-free conditions. This protocol proceeds via the functi
Metal-free oxidative radical addition of carbonyl compounds to a,a-Diaryl allylic alcohols: Synthesis of highly functionalized Ketones
Chu, Xue-Qiang,Meng, Hua,Zi, You,Xu, Xiao-Ping,Ji, Shun-Jun
supporting information, p. 17198 - 17206 (2015/01/09)
A metal-free direct alkylation of simple carbonyl compounds (ketones, esters, and amides) with a,a-diaryl allylic alcohols is described. The protocol provides facile access to highly functionalized dicarbonyl ketones by a radical addition/1,2-aryl migration cascade. The regioselectivity of the reaction was precisely controlled by the nature of the carbonyl compound.
Photoaddition of styrene on certain β-polyketones
Mansri, Ali,Casals, Pierre-Francois,Fan, Bo Tao,Lapluye, Gerard
, p. 247 - 252 (2007/10/02)
The irradiation of 1,5-diphenylpentane-1,3,5-trione 1 and 1-phenylhexane-1,3,5-trione 2 at λ > 290 nm with styrene gives products of double photo-addition: 1,2,6,9-tetraphenylnonane-1,5,9-trione 5 and 1,2,6-triphenyldecane-1,5,9-trione 6, respectively.Under the same conditions with λ > 220 nm, 2-(3-oxo-3-phenylpropionyl)indane-1,3-dione 3 and 2-(3-oxobutyryl)indane-1,3-dione 4 give only products of simple photoaddition: 4-(3-oxo-3-phenylpropionyl)-2-phenylbenzocycloheptane-1,5-dione 7 and 4-(3-oxobutyryl)-2-phenylbenzocycloheptane-1,5-dione 8, respectively.The regiospecificity previously observed with the β-diketones is not a general rule for these β-triketones.The phenyl group in position 6 (products 5 and 6) is not in the α-position of the benzoyl group.The δ-triketones obtained are characterized using β-diketonic models, which are prepared by a simple sequence.Observations of products 7 and 8 show that styrene reacts with the cyclic enol only.This work may be considered as a model study for the prediction of the behavior of triketones 1, 2, 3 and 4 in the side chain of polymeric compounds.Keywords: photoaddition / styrene / β-polyketones / stereoselectivity
