TY - JOUR
T1 - Macrocyclic Transformations from Norrole to Isonorrole and an N-Confused Corrole with a Fused Hexacyclic Ring System Triggered by a Pyrrole Substituent
AU - Li, Miao
AU - Wei, Pingchun
AU - Ishida, Masatoshi
AU - Li, Xin
AU - Savage, Mathew
AU - Guo, Rui
AU - Ou, Zhongping
AU - Yang, Sihai
AU - Furuta, Hiroyuki
AU - Xie, Yongshu
N1 - Funding Information:
This work was supported by the Science Fund for Creative Research Groups (21421004), the NSFC/China (21472047 and 91227201), the National Basic Research 973 Program (2013CB733700), the Oriental Scholarship, the Programme of Introducing Talents of Discipline to Universities (B16017), and JSPS Grant-in-Aid for Scientific Research (25248039 and 26810024).
Publisher Copyright:
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA.
PY - 2016/2/24
Y1 - 2016/2/24
N2 - Three kinds of fused porphyrinoids, L2-L4, possessing different types of corrole-based frameworks were synthesized from a pyrrole-substituted corrole isomer (norrole L1). Oxidation of L1 afforded a unique N-Cmeso-fused pyrrolyl isonorrole L2, involving the fusion of an auxiliary pyrrolic NH moiety with a meso-sp3-hybridized carbon atom. Subsequently, L2 underwent macrocycle transformations to give singly and doubly N-CAr-fused N-confused corroles, L3 and L4, respectively. L3 and L4 contain fused [5.7.6.5]-tetra- and [5.6.7.7.6.5]-hexacyclic structures, respectively, prepared through lateral annulation. These skeletal transformation reactions from norrole to its isomer isonorrole and finally to N-confused corrole indicate that multiply fused porphyrinoids could be readily synthesized from pyrrole-appended confused porphyrinoids.
AB - Three kinds of fused porphyrinoids, L2-L4, possessing different types of corrole-based frameworks were synthesized from a pyrrole-substituted corrole isomer (norrole L1). Oxidation of L1 afforded a unique N-Cmeso-fused pyrrolyl isonorrole L2, involving the fusion of an auxiliary pyrrolic NH moiety with a meso-sp3-hybridized carbon atom. Subsequently, L2 underwent macrocycle transformations to give singly and doubly N-CAr-fused N-confused corroles, L3 and L4, respectively. L3 and L4 contain fused [5.7.6.5]-tetra- and [5.6.7.7.6.5]-hexacyclic structures, respectively, prepared through lateral annulation. These skeletal transformation reactions from norrole to its isomer isonorrole and finally to N-confused corrole indicate that multiply fused porphyrinoids could be readily synthesized from pyrrole-appended confused porphyrinoids.
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U2 - 10.1002/anie.201510879
DO - 10.1002/anie.201510879
M3 - Article
AN - SCOPUS:84958839793
VL - 55
SP - 3063
EP - 3067
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 9
ER -