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Synthesis of 2‐Arylphenol Derivatives through a One‐Pot Suzuki–Miyaura Coupling/Dehydrogenative Aromatization Sequence with Pd/C Catalysis
Author(s) -
Kikushima Kotaro,
Nishina Yuta
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.201500723
Subject(s) - chemistry , aromatization , catalysis , phenols , one pot synthesis , substrate (aquarium) , combinatorial chemistry , organic chemistry , suzuki reaction , palladium , oceanography , geology
Abstract One‐pot synthesis of 2‐arylphenols starting from 2‐iodo‐2‐cyclohexen‐1‐one and arylboronic acids through sequential Suzuki–Miyaura coupling/dehydrogenative aromatization with Pd/C catalysis has been developed. A range of arylboronic acids serve as substrates, including those containing electron‐donating or electron‐withdrawing groups. Additionally, one‐pot synthesis of di‐ or trisubstituted phenols bearing a phenyl group at the ortho position are also generated by using 2‐iodo‐2‐cyclohexen‐1‐one derivatives as substrate. In the present method, commercially available and easily removable Pd/C was employed as a catalyst without any ligands. The operationally simple procedure and accessible conditions were used to provide modified phenols as the sole product in moderate to high yields.