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Gold‐Catalyzed One‐Pot A 3 ‐Coupling/1,5‐Hydride Shift/Schmittel‐Type Cyclization: From Aldehydes, Amines and Alkynes to the Synthesis of Benzo[ b ]fluorenes
Author(s) -
Lustosa Danilo M.,
Hartmann Deborah,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2020
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.201901906
Subject(s) - chemistry , allene , catalysis , hydride , medicinal chemistry , organic chemistry , metal
A step‐economic gold‐catalyzed one‐pot synthesis of benzo[ b ]fluorenes, from aldehydes, alkynes and amines, proceeding via an A 3 ‐coupling/1,5‐hydride shift/Schmittel‐type cyclization is described. The formation of the allene intermediate is not dependent on a previous installation of reaction triggers, and upon cyclization delivered benzo[ b ]fluorenes. With this method, just by an easy modification of the starting materials in a modular way, nineteen benzo[ b ]fluorenes, bearing different substituents Ar 1 , Ar 2 and Ar 3 , were prepared. Overall, three new carbon–carbon bonds are formed in one‐pot.