Benzannulation of isobenzopyryliums with electron-rich alkynes: a modular access to β-functionalized naphthalenes. Issue 30 (15th July 2020)

• Record Type: Journal Article
• Authors: Wu, An; Qian, Hui; Zhao, Wanxiang; Sun, Jianwei
• Is Part Of: Chemical science. Volume 11:Issue 30(2020)
• Page Start: 7957
• Page End: 7962
• Publication Date: 2020-07-15
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0sc02502j
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A substituent-controlled divergent benzannulation provides rapid access to various β-functionalized naphthalenes from electron-rich alkynes. Abstract : Described here is a modular strategy for the rapid synthesis of β-functionalized electron-rich naphthalenes, a family of valuable molecules lacking general access previously. Our approach employs an intermolecular benzannulation of in situ generated isobenzopyrylium ions with various electron-rich alkynes, which were not well utilized for this type of reaction before. These reactions not only feature a broad scope, complete regioselectivity, and mild conditions, but also exhibit unusual product divergence depending on the substrate substitution pattern. This divergence allows further expansion of the product diversity. Control experiments provided preliminary insights into the reaction mechanism.