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Gram‐Scale Synthesis of the 1,1, n , n ‐Tetramethyl[ n ](2,11)teropyrenophanes
Author(s) -
Unikela Kiran Sagar,
Ghasemabadi Parisa Ghods,
Houska Václav,
Dawe Louise N.,
Zhao Yuming,
Bodwell Graham J.
Publication year - 2021
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.202003828
Subject(s) - gram , halogenation , alkylation , chemistry , scale (ratio) , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , bacteria , physics , biology , genetics , quantum mechanics
A gram‐scale synthesis of a series of 1,1, n , n ‐tetramethyl[ n ](2,11)teropyrenophanes ( n= 7–9) has been accomplished as well as the first synthesis of the next higher homologue 1,1,10,10‐tetramethyl[10](2,11)teropyrenophane. The scale‐up of the original small‐scale synthesis required the development of several heavily modified synthetic methods, including a chlorination/Friedel–Crafts alkylation protocol and an iodination/Wurtz coupling protocol, which were performed on 25–30 g and 30–60 g scales, respectively. Two separate sets of conditions for the key teropyrene‐forming cyclodehydrogenation reaction at the end of the synthetic pathway were developed, an acid‐promoted one for the two less strained congeners and an acid‐free method for the two more strained homologues.