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Gold(I)‐Catalyzed Allene–Diene–Alkyne Coupling Reaction to Polycycles
Author(s) -
Semleit Nina,
Kreuzahler Mathis,
Haberhauer Gebhard
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.202001190
Subject(s) - allene , alkyne , chemistry , diene , catalysis , coupling reaction , combinatorial chemistry , reaction mechanism , photochemistry , computational chemistry , organic chemistry , natural rubber
In general, the design of complex polycycles from simple building blocks is challenging and requires many reaction steps. Herein, we present that complex polycycles can be synthesized starting from two alkyne building blocks in a one‐pot reaction using gold(I) as catalyst, in yields up to 77 %. Mechanistically, the process can be described as cascade reaction in two steps: first, the allene is formed by gold(I)‐catalyzed dearomatization, second, the desired product is then obtained by allene–diene–alkyne coupling. Quantum chemical investigations confirm the assumed mechanism. In sum, five new C–C bonds are built in one sweep, which is extraordinary since non‐identical building blocks are combined in this reaction. The introduced new allene–diene–alkyne coupling reaction paves the way for several new syntheses of cycles and polycycles considering potential intermolecular reactions.