1,2,3- versus 1,2-Indeno Ring Fusions Influence Structure Property and Chirality of Corannulene Bowls | Zendy

Shi Liu | Zendy; Loı̈c M. Roch | Zendy; Oliver Allemann | Zendy; Jun Xu | Zendy; Nicolas Vanthuyne | Zendy; Kim K. Baldridge | Zendy; Jay S. Siegel | Zendy

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1,2,3- versus 1,2-Indeno Ring Fusions Influence Structure Property and Chirality of Corannulene Bowls

Author(s) -

Shi Liu,

Loı̈c M. Roch,

Oliver Allemann,

Jun Xu,

Nicolas Vanthuyne,

Kim K. Baldridge,

Jay S. Siegel

Publication year - 2018

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.8b00320

Subject(s) - chemistry , enantiopure drug , corannulene , ring (chemistry) , crystal structure , stereochemistry , chirality (physics) , aryl , crystallography , catalysis , enantioselective synthesis , molecule , organic chemistry , chiral symmetry breaking , physics , alkyl , quantum mechanics , quark , nambu–jona lasinio model

Annulated corannulenes 3-5 form via distinct synthetic pathways: (i) Pd-catalyzed sp 3 CH insertion, (ii) Pd-catalyzed aryl coupling, and (iii) silyl cation-promoted C-F activation/CH insertion. Crystal structure, redox, and photophysical studies elucidate the differing influence of 1,2,3- versus 1,2-indeno ring fusions. Mono and dianions of 3-5 are characterized. Resolution of 4 gives enantiopure forms, allowing assessment of the bowl-inversion barrier.

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