Binary additive effect of benzoic acid in ipso-Friedel-Crafts-type dearomatization of phenols using a chiral silver phosphate. (Downloadable article, 2018) [WorldCat.org]
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Binary additive effect of benzoic acid in ipso-Friedel-Crafts-type dearomatization of phenols using a chiral silver phosphate.

Author: Hiroki Nakayama; Shingo Harada; Ayaka Kanda; Irene Mei-Yi Kwok; Tetsuhiro Nemoto
Publisher: [Oxford] : Pergamon Press, 2018.
Edition/Format:   Downloadable article : Document   Computer File : English
Publication:Tetrahedron
Summary:
Abstract: We previously developed a chemoselective asymmetric phenol dearomatization using a silver catalyst and benzoic acid as an additive to enhance the reaction efficiency. The mechanistic role of the additive, however, remained unclear. Herein we describe detailed studies to elucidate the additive effect, which revealed that benzoic acid plays two supporting roles in the silver-catalyzed reaction. First, it  Read more...
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Details

Material Type: Document, Internet resource
Document Type: Internet Resource, Article, Computer File
All Authors / Contributors: Hiroki Nakayama; Shingo Harada; Ayaka Kanda; Irene Mei-Yi Kwok; Tetsuhiro Nemoto
ISSN:0040-4020
OCLC Number: 1051884285
Notes: In: Tetrahedron, Vol. 74, no. 20 (2018), p.2435-2439.
Description: 1 online resource

Abstract:

Abstract: We previously developed a chemoselective asymmetric phenol dearomatization using a silver catalyst and benzoic acid as an additive to enhance the reaction efficiency. The mechanistic role of the additive, however, remained unclear. Herein we describe detailed studies to elucidate the additive effect, which revealed that benzoic acid plays two supporting roles in the silver-catalyzed reaction. First, it promotes protonation of a silver enolate intermediate to improve the chemical yield of a spirolactam. Second, it dissociates a homochiral dimer of silver phosphate to generate a monomeric species. Graphical abstract

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