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Palladium‐Catalyzed Cascade Reaction of o ‐Bromobenzaldehydes with N ‐Sulfonylhydrazones: An Efficient Approach to the Naphthalene Skeleton
Author(s) -
Zhang Heng,
Yu Yinghua,
Huang Shenlin,
Huang Xueliang
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801637
Subject(s) - chemistry , palladium , intramolecular force , naphthalene , sulfonyl , catalysis , tsuji–trost reaction , carbene , cascade , combinatorial chemistry , alkylation , cascade reaction , medicinal chemistry , photochemistry , organic chemistry , alkyl , chromatography
A new strategy for the construction of the naphthalene backbone is described. The reaction essentially starts from two simple aldehydes. The key step is enabled by a palladium‐carbene migratory insertion. After that, a sequence of reversible allylic alkylation and intramolecular condensation takes place to give the substituted naphthalene derivatives. Additional manipulations on the sulfonyl group in the product via palladium‐catalyzed Kumada coupling were also investigated.