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Efficient Synthesis of β‐Alkynylcorroles
Author(s) -
Stefanelli Manuela,
Naitana Mario L.,
Chiarini Marco,
Nardis Sara,
Ricci Antonella,
Fronczek Frank R.,
Lo Sterzo Claudio,
Smith Kevin M.,
Paolesse Roberto
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501138
Subject(s) - sonogashira coupling , stille reaction , corrole , chemistry , regioselectivity , alkyne , halogenation , combinatorial chemistry , yield (engineering) , organic chemistry , palladium , catalysis , materials science , metallurgy
The introduction of alkynyl groups at the β‐pyrrolic positions of dibrominated corrole derivatives was attempted by using both Sonogashira and Stille coupling methodologies. An efficient bromination protocol was developed by using a silver corrolate, which enabled the regioselective preparation of the 3,17‐Br 2 isomer in high yield. Whereas unsatisfactory results were obtained by applying Sonogashira reaction conditions, the Stille methodology produced, for the first time, novel 3,17‐diphenylethynylcorrole derivatives in good to excellent yields. A mild demetalation protocol of the silver complex led to the corresponding corrole free base, opening the way for the preparation of different metal complexes and further elaboration of the corrole platform by using alkyne chemistry.