Access to Multifunctionalized Benzofurans by Aryl Nickelation of Alkynes: Efficient Synthesis of the Anti-Arrhythmic Drug Amiodarone
Dr. Naeem Iqbal
Department of Chemistry, Chung-Ang University, 84 Heukseok-ro, Dongjak-gu, Seoul, 06974 Republic of Korea
Search for more papers by this authorNaila Iqbal
Department of Chemistry, Chung-Ang University, 84 Heukseok-ro, Dongjak-gu, Seoul, 06974 Republic of Korea
Search for more papers by this authorCorresponding Author
Prof. Dr. Debabrata Maiti
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400076 India
Search for more papers by this authorCorresponding Author
Prof. Dr. Eun Jin Cho
Department of Chemistry, Chung-Ang University, 84 Heukseok-ro, Dongjak-gu, Seoul, 06974 Republic of Korea
Search for more papers by this authorDr. Naeem Iqbal
Department of Chemistry, Chung-Ang University, 84 Heukseok-ro, Dongjak-gu, Seoul, 06974 Republic of Korea
Search for more papers by this authorNaila Iqbal
Department of Chemistry, Chung-Ang University, 84 Heukseok-ro, Dongjak-gu, Seoul, 06974 Republic of Korea
Search for more papers by this authorCorresponding Author
Prof. Dr. Debabrata Maiti
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400076 India
Search for more papers by this authorCorresponding Author
Prof. Dr. Eun Jin Cho
Department of Chemistry, Chung-Ang University, 84 Heukseok-ro, Dongjak-gu, Seoul, 06974 Republic of Korea
Search for more papers by this authorGraphical Abstract
An unconventional nickel-catalyzed reaction has been developed for the synthesis of multifunctionalized benzofurans through the aryl nickelation of alkynes. A nucleophilic vinyl NiII species, from regioselective syn-aryl nickelation of an alkyne, undergoes an intramolecular cyclization with phenol ester to yield highly functionalized 1,1-disubstituted alkenes with 3-benzofuranyl and (hetero)aryl substituents.
Abstract
An unconventional nickel-catalyzed reaction was developed for the synthesis of multifunctionalized benzofurans from alkyne-tethered phenolic esters. The transformation involves the generation of a nucleophilic vinyl NiII species by the regioselective syn-aryl nickelation of an alkyne, which then undergoes an intramolecular cyclization with phenol ester to yield highly functionalized 1,1-disubstituted alkenes with 3-benzofuranyl and (hetero)aryl substituents. The methodology can be used for the late-stage benzofuran incorporation of various drug molecules and natural products, such as 2-propylvaleric acid, gemfibrozil, biotin, and lithocholic acid. Furthermore, this arylative cyclization method was successfully applied for the efficient synthesis of the anti-arrhythmic drug amiodarone.
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