Open AccessInvestigation of the K4[Fe(CN)6]-Mediated Mono- and Bis-Palladium-Catalyzed Cyanation of the Benzothioxanthene Core
Author(s) -
Pablo Simón Marqués,
José María Andrés Castán,
Laura Abad Galán,
Magali Allain,
Olivier Maury,
Tangui Le Bahers,
Philippe Blanchard,
Clément Cabanetos
Publication year - 2021
Publication title -
the journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.1c00318
Subject(s) - cyanation , chemistry , palladium , nitrile , catalysis , imide , deuterium , derivative (finance) , electrochemistry , structural isomer , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , electrode , physics , quantum mechanics , financial economics , economics
The pallado-catalyzed cyanation of benzothioxanthene imide ( BTXI ) derivatives is explored herein. Once optimized on the monobromo BTXI , mild reaction conditions were successfully applied to the dibromo derivative affording two regioisomers that have been isolated and structurally solved. Additional hydrogen-deuterium exchange experiments were carried out to support a proposed mechanism involving the formation of a five-membered palladacycle intermediate in the bay area. As well as impacting the structural, photo physical and electrochemical properties of the BTXI core, nitrile moieties were successfully used as orthogonal protecting groups, thus opening doors to new design principles.
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