TY - JOUR
T1 - Radical-Enabled Bicyclization Cascades of Oxygen-Tethered 1,7-Enynes Leading to Skeletally Diverse Polycyclic Chromen-2-ones
AU - Jiang, Bo
AU - Li, Jie
AU - Pan, Yuanyuan
AU - Hao, Wenjuan
AU - Li, Guigen
AU - Tu, Shujiang
N1 - Publisher Copyright:
© 2017 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2017/3
Y1 - 2017/3
N2 - 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.
AB - 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.
KW - 1,7-enynes
KW - C(sp)-H functionalization
KW - bicyclization
KW - fused chromen-2-ones
KW - radical reaction
UR - http://www.scopus.com/inward/record.url?scp=85013298134&partnerID=8YFLogxK
U2 - 10.1002/cjoc.201600571
DO - 10.1002/cjoc.201600571
M3 - Article
AN - SCOPUS:85013298134
VL - 35
SP - 323
EP - 334
JO - Chinese Journal of Chemistry
JF - Chinese Journal of Chemistry
SN - 1001-604X
IS - 3
ER -