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Fe‐Catalyzed Intramolecular Cross‐Dehydrogenative Arylation (CDA), Efficient Synthesis of 1‐Arylnaphthalenes and 4‐Arylcoumarins
Author(s) -
Diao Haiyan,
Wang Changcheng,
Zhang Zhen,
Shi Zhangjie,
Liu Feng
Publication year - 2021
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.202100056
Subject(s) - chemistry , dehydrogenation , intramolecular force , tandem , yield (engineering) , catalysis , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , materials science , metallurgy , composite material
Direct cross‐dehydrogenative coupling of different inert C−H bonds is the most straightforward and environmentally benign method to construct C−C bonds. In this paper, we developed an iron‐catalyzed intramolecular cross‐dehydrogenative arylation (CDA) between benzylic C( sp 3 )H bond and aromatic C( sp 2 )H bond. From the readily available linear substrates, 1‐arylnaphthalenes and 4‐arylcoumarins can be quickly constructed with moderate to good yield (18 examples, up to 73 % yield) in one step. Both symmetrical and unsymmetrical substrates with different functional groups could tolerate this system well to form the anticipated products. A radical initiated dehydrogenative cyclization‐dehydrogenation tandem process was proposed.