94540-12-2Relevant academic research and scientific papers
Asymmetric Synthesis of 1,2-Dihydronaphthalene-1-ols via Copper-Catalyzed Intramolecular Reductive Cyclization
Acharyya, Ranjan Kumar,Kim, Soyoung,Park, Yeji,Han, Jung Tae,Yun, Jaesook
supporting information, p. 7897 - 7902 (2020/11/02)
We describe a copper-catalyzed intramolecular reductive cyclization of easily accessible benz-tethered 1,3-dienes containing a ketone moiety. This process provided biologically active 1,2-dihydronaphthalene-1-ol derivatives in good yields with excellent enantio- and diastereoselectivity. Mechanistic investigations using density functional theory revealed that (Z)- and (E)-allylcopper intermediates formed in situ from the diene and copper catalyst undergo isomerization and selective intramolecular allylation of the (E)-allylcopper form of the major product through a six-membered boatlike transition state. The resulting products were further transformed to fully saturated naphthalene-1-ols by reactions of the olefin moiety.
Synthesis of Substituted Naphthalenes by 1,4-Palladium Migration Involved Annulation with Internal Alkynes
Wei, Dong,Hu, Tian-Jiao,Feng, Chen-Guo,Lin, Guo-Qiang
supporting information, p. 743 - 748 (2018/07/25)
The palladium catalyzed annulation of 1-bromo-2-vinylbenzene derivatives with internal alkynes was realized for the efficient synthesis of substituted naphthalenes. A controllable aryl to vinylic 1,4-palladium migration process is the key for success.
Polycyclic Aromatic Hydrocarbons via Iron(III)-Catalyzed Carbonyl-Olefin Metathesis
McAtee, Christopher C.,Riehl, Paul S.,Schindler, Corinna S.
, p. 2960 - 2963 (2017/03/11)
Polycyclic aromatic hydrocarbons are important structural motifs in organic chemistry, pharmaceutical chemistry, and materials science. The development of a new synthetic strategy toward these compounds is described based on the design principle of iron(III)-catalyzed carbonyl-olefin metathesis reactions. This approach is characterized by its operational simplicity, high functional group compatibility, and regioselectivity while relying on FeCl3 as an environmentally benign, earth-abundant metal catalyst. Experimental evidence for oxetanes as reactive intermediates in the catalytic carbonyl-olefin ring-closing metathesis has been obtained.
Borylation of Olefin C-H Bond via Aryl to Vinyl Palladium 1,4-Migration
Hu, Tian-Jiao,Zhang, Ge,Chen, Ya-Heng,Feng, Chen-Guo,Lin, Guo-Qiang
supporting information, p. 2897 - 2900 (2016/03/19)
The aryl to vinyl palladium 1,4-migration was realized for the first time. The generated alkenyl palladium species was trapped by diboron reagents under Miyaura borylation conditions, providing a new method to synthesize β,β-disubstituted vinylboronates. The excellent regioselectivity and broad substrate scope were observed for this novel transformation.
