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Radical‐Enabled Bicyclization Cascades of Oxygen‐Tethered 1,7‐Enynes Leading to Skeletally Diverse Polycyclic Chromen‐2‐ones
Author(s) -
Jiang Bo,
Li Jie,
Pan Yuanyuan,
Hao Wenjuan,
Li Guigen,
Tu Shujiang
Publication year - 2017
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201600571
Subject(s) - chemistry , functional group , aryl , catalysis , oxygen , combinatorial chemistry , oxygen atom , stereochemistry , molecule , organic chemistry , alkyl , polymer
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(sp 3 )‐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.