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Gram‐Scale Synthesis and Highly Regioselective Bromination of 1,1,9,9‐Tetramethyl[9](2,11)teropyrenophane
Author(s) -
Unikela Kiran Sagar,
Roemmele Tracey L.,
Houska Václav,
McGrath Kaitlin E.,
Tobin David M.,
Dawe Louise N.,
Boeré René T.,
Bodwell Graham J.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201713067
Subject(s) - halogenation , regioselectivity , gram , alkylation , chemistry , coupling reaction , combinatorial chemistry , organic chemistry , catalysis , bacteria , biology , genetics
An improved synthetic pathway to the nanobelt‐like 1,1,9,9‐tetramethyl[9](2,11)teropyrenophane has been developed, and enables the synthesis of gram quantities of material. Key innovations are the development of a sequential chlorination/Friedel–Crafts alkylation reaction, a sequential iodination/Wurtz coupling reaction, and a room‐temperature teropyrene‐forming reaction. The teropyrenophane was found to form a very stable radical cation and undergo a completely regioselective fourfold bromination reaction.