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Cyclopenta[b]thiopyran and cyclopenta[b]selenopyran based heteroarenes: electronic communication between S- and/or Se-fused aromatics.
Chem Commun (Camb)
April 2019
Lab of Advanced Materials, State Key Laboratory of Molecular Engineering of Polymers, Fudan University, Shanghai 200438, P. R. China.
S- and Se-heteroarenes containing cyclopenta[b]thiopyran and/or cyclopenta[b]selenopyran moieties have been synthesized via PtCl2-catalyzed ring-expanding cycloaromatizations. Intervalence charge transfer bands can be observed for the three heteroarenes upon chemical oxidation, suggesting the electronic communication between S- and/or Se-fused aromatics.
View Article and Find Full Text PDFSynthesis and Molecular Properties of Two Isomeric Dialkylated Tetrathienonaphthalenes.
Org Lett
February 2016
Department of Applied Chemistry, National Chiao Tung University , 1001 University Road, Hsin-Chu, Taiwan.
Isomeric 2,8-distannyl 5,11-didodecyl αβ-TTN (1, tetrathienonaphthalene = TTN) and 2,8-didodecyl 5,11-distannyl αβ-TTN (2) have been designed and successfully synthesized. The naphthalene core structures in αβ-TTNs were constructed by a systematic protocol using PtCl2-catalyzed cyclization followed by oxidative Scholl annulation in good yields. Compared to the one-dimensional naphthodithiophene derivatives, the two-dimensional αβ-TTN molecules showed good solubility, extended conjugation, strong absorptivity, and highly coplanar structures.
View Article and Find Full Text PDFCyclobutene formation in PtCl2-catalyzed cycloisomerizations of heteroatom-tethered 1,6-enynes.
Chemistry
September 2014
Aix-Marseille Université, Centrale Marseille, CNRS, ISm2, UMR 7313, 13397 Marseille (France).
Aza(oxa)bicyclo[3.2.0]heptenes are accessed through the PtCl2 -catalyzed cycloisomerizations of heteroatom-tethered 1,6-enynes featuring a terminal alkyne and amide as the solvent.
View Article and Find Full Text PDFStudies on [PtCl2 ]- or [AuCl]-catalyzed cyclization of 1-(Indol-2-yl)-2,3-allenols: the effects of water/steric hindrance and 1,2-migration selectivity.
Chemistry
August 2014
Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang (P.R. China).
The [PtCl2 ]- or [AuCl]-catalyzed reaction of 1-(indol-2-yl)-2,3-allenols occurred smoothly at room temperature to afford a series of poly-substituted carbazoles efficiently. Compared with the [PtCl2 ]-catalyzed process, the [AuCl]-catalyzed reaction represents a significant advance in terms of the scope and the selectivity. Selective 1,2-alkyl or aryl migration of the gold carbene intermediate was observed: compared with the methyl group, the isopropyl, cyclopropyl, cyclobutyl, and cyclohexyl groups migrate exclusively; the cyclopropyl group shifts selectively over the ethyl group; the 1,2-migration of a non-methyl linear alkyl is faster than methyl group; the phenyl group migrates exclusively over methyl or ethyl group.
View Article and Find Full Text PDFMechanisms of the PtCl2-catalyzed intramolecular cyclization of o-isopropyl-substituted aryl alkynes for the synthesis of indenes and comparison of three sp3 C-H bond activation modes.
J Org Chem
June 2014
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China.
Chatani and He respectively reported an efficient way to synthesize indenes through PtCl2 catalyzed sp(3) C-H bond activation. Interestingly, the R group (R = H or Br) in the alkyne moiety of the substrates in Chatani's experiments migrates to the C3 position in indenes, whereas the R group (R = Ar) stays in the original C2 position of final indenes in He's experiments. DFT calculations indicated that there are two competing pathways a and c for the cyclization reaction.
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