Secondary amine-catalyzed [3 + 3] benzannulation to access polysubstituted benzenes through iminium activation. Issue 3 (1st February 2018)

• Record Type: Journal Article
• Authors: Jiang, Lin; Li, Hang; Zhou, Jiang-Feng; Yuan, Ming-Wei; Li, Hong-Li; Chuan, Yong-Ming; Yuan, Ming-Long
• Is Part Of: Synthetic communications. Volume 48:Issue 3(2018)
• Page Start: 336
• Page End: 343
• Publication Date: 2018-02-01
• Subjects: [3 + 3] Benzannulation -- aminocatalysis -- biaryl sulfones -- iminium activation -- polysubstituted benzenes; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2017.1402351
• Languages: English
• ISSNs: 0039-7911

Abstract

ABSTRACT: An organocatalytic [3 + 3] benzannulation to access polysubstituted benzenes from readily availableα, β -unsaturated aldehydes and 1, 3-bis(phenylsulfonyl)propene or 4-sulfonylcrotonates is described. The key reaction step is considered to be the iminium activation of enals by a secondary aminocatalyst. This organocatalytic protocol avoids the traditional strategy which is always with the aid of a transition-metal or a stoichiometric amount of strong base, and allows the synthesis of trisubstituted benzenes in high to excellent yields (74–96%). GRAPHICAL ABSTRACT: