A photoinduced arene–alkyne [3 + 2] cycloaddition cascade of 1-alkynylnaphthalen-2-ols for tunable synthesis of skeletally diverse bridged hexacycles. Issue 9 (1st March 2021)

• Record Type: Journal Article
• Authors: Zhu, Chi-Fan; Zhang, Jie; Zhu, Yi-Long; Hao, Wen-Juan; Tu, Shu-Jiang; Wang, De-Cai; Jiang, Bo
• Is Part Of: Organic chemistry frontiers. Volume 8:Issue 9(2021)
• Page Start: 1952
• Page End: 1958
• Publication Date: 2021-03-01
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo00124h
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : Photoinduced solvent-dependent cyclodimerizations of 1-alkynylnaphthalen-2-ols were developed for the first time, producing skeletally diverse bridged hexacyclic architectures with good yields and high stereoselectivities. Abstract : Photoinduced arene–alkyne [3 + 2] cycloaddition cascades of 1-alkynylnaphthalen-2-ols without a photosensitizer were developed for the first time, enabling tunable synthesis of skeletally diverse bridged hexacyclic architectures with good yields and complete stereoselectivities through solvent-dependent divergent dearomatized cyclodimerizations. The photocatalysis in N, N -dimethylformamide (DMF) delivered functionalized bicyclo[3.2.1]octane-containing bridged oxa-heterocycles, whereas tetrahydrofuran (THF) oriented high stereoselectivity to offer bridged carbocycles. The reaction pathway generates two classes of complex three-dimensional structures that evolve from the same planar internal alkynes.