Literature DB >> 16836357

Friedel-Crafts-type cyclization of 2,2-difluorovinyl ketones via alpha-fluorocarbocations and its application in domino cyclizations.

Junji Ichikawa1, Mikio Kaneko, Misaki Yokota, Masaaki Itonaga, Takaharu Yokoyama.   

Abstract

[Structure: see text] 2,2-Difluorovinyl ketones bearing an aryl group undergo Friedel-Crafts-type cyclization via carbocations stabilized by alpha-fluorines on treatment with a trimethylsilylating agent [Me3SiOTf or Me3SiB(OTf)4]. The reaction affords 4-fluorinated 3-acyl-1,2-dihydronaphthalenes, which are successfully subjected to a substitution-cyclodehydration process or a Nazarov-type cyclization to construct fused polycyclic systems.

Entities:  

Year:  2006        PMID： 16836357     DOI： 10.1021/ol060912r

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  3 in total

1.  Radical Chlorodifluoromethylation: Providing a Motif for (Hetero)arene Diversification.

Authors:  Rory C McAtee; Joel W Beatty; Christopher C McAtee; Corey R J Stephenson
Journal:  Org Lett       Date:  2018-06-01       Impact factor: 6.005

2.  Ring-size-selective construction of fluorine-containing carbocycles via intramolecular iodoarylation of 1,1-difluoro-1-alkenes.

Authors:  Takeshi Fujita; Ryo Kinoshita; Tsuyoshi Takanohashi; Naoto Suzuki; Junji Ichikawa
Journal:  Beilstein J Org Chem       Date:  2017-12-14       Impact factor: 2.883

3.  Synthesis of aryl 2-bromo-2-chloro-1,1-difluoroethyl ethers through the base-mediated reaction between phenols and halothane.

Authors:  Yukiko Karuo; Ayaka Kametani; Atsushi Tarui; Kazuyuki Sato; Kentaro Kawai; Masaaki Omote
Journal:  Beilstein J Org Chem       Date:  2021-01-11       Impact factor: 2.883
  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.