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Intramolecular Oxidative Arylations in 7‐Azaindoles and Pyrroles: Revamping the Synthesis of Fused N ‐Heterocycle Tethered Fluorenes
Author(s) -
Laha Joydev K.,
Bhimpuria Rohan A.,
Hunjan Mandeep Kaur
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604192
Subject(s) - intramolecular force , fluorene , chemistry , steric effects , pyrrole , combinatorial chemistry , oxidative phosphorylation , stereochemistry , organic chemistry , polymer , biochemistry
We revealed intramolecular oxidative arylations in 7‐azaindoles and pyrroles that, for the first time, provided direct access to 7‐azaindole‐ or pyrrole‐fused isoindolines and tetrahydroisoquinolines. In addition, N‐benzylation of 7‐azaindoles or pyrroles with sterically hindered sec ‐benzyl alcohols by Mitsunobu reaction followed by intramolecular oxidative arylation allowed access to chiral congeners of fused isoindolines that have little precedence. A new opportunity in the design and synthesis of fluorene‐based organic emitters is demonstrated in the preparation of novel fused N ‐heterocycle tethered fluorenes, including a chiral fluorene architecture.