Gram‐Scale Synthesis and Highly Regioselective Bromination of 1,1,9,9‐Tetramethyl[9](2,11)teropyrenophane | Zendy

Unikela Kiran Sagar | Zendy; Roemmele Tracey L. | Zendy; Houska Václav | Zendy; McGrath Kaitlin E. | Zendy; Tobin David M. | Zendy; Dawe Louise N. | Zendy; Boeré René T. | Zendy; Bodwell Graham J. | Zendy

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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

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201713067

Subject(s) - halogenation , regioselectivity , chemistry , alkylation , coupling reaction , combinatorial chemistry , gram , organic chemistry , catalysis , biology , bacteria , 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.

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