Radical-Enabled Bicyclization Cascades of Oxygen-Tethered 1,7-Enynes Leading to Skeletally Diverse Polycyclic Chromen-2-ones

作     者：Bo Jiang Jie Li Yuanyuan Pan Wenjuan Hao Guigen Li Shujiang Tu 

作者机构：School of Chemistry and Chemical Engineering Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials Jiangsu Normal University Xuzhou Jiangsu 221116 China Department of Chemistry and Biochemistry Texas Tech University Lubbock Texas 79409-1061 United States Institute of Chemistry & BioMedical Sciences Collaborative Innovation Center of Chemistry for Life Sciences Nanjing University Nanjing Jiangsu 210093 China 

出 版 物：《Chinese Journal of Chemistry》 (中国化学（英文版）)

年 卷 期：2017年第35卷第3期

页      面：323-334页

核心收录：

学科分类：07[理学] 

基　　金：国家自然科学基金 江苏高校优势学科建设工程 the Outstanding Youth Fund of Jiangsu Normal University 江苏省自然科学基金 the Natural Science Foundation of JSNU the Qing Lan Project and NSF of Jiangsu Education Committee 

主　　题：bicyclization radical reaction 1 7-enynes fused chromen-2-ones C(sp³)-H functionalization 

摘      要：Catalytic bicyclization cascades of oxygen-tethered 1,7-enynes with simple cycloalkanes or aryl sulfonhydrazides have been established via subsequent multiple C-C bond-forming events from alkynyl/alkenyl functions, delivering a series of densely functionalized tetracyclic chromen-2-ones in a functional-group-compatible manner. In the former, Fe-catalyzed spiro-bicyclization involves radical addition, 6-exo-dig cyclization, H-abstraction and 5-endo-trig cyclization sequences under mild conditions, resulting in new spiro-fused cyclopenta[c]chromen-2-ones via dual α,α-C(sp3)-H abstractions. The latter enables in-situ sulfonylation and desulfonylation of oxygen-tethered 1,7-enynes to realize the construction of multiple C-C bonds, thereby leading to the formation of naphtho[2,3-c]chromen-6-ones.