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Formal anti ‐Carbopalladation Reactions of Non‐Activated Alkynes: Requirements, Mechanistic Insights, and Applications
Author(s) -
Pawliczek Martin,
Schneider Tobias F.,
Maaß Christian,
Stalke Dietmar,
Werz Daniel B.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201411210
Subject(s) - intramolecular force , isomerization , chemistry , combinatorial chemistry , stereochemistry , catalysis , organic chemistry
Formal anti‐carbopalladation reactions of CC triple bonds are uncommon, but highly useful transformations. Alkynes can be designed to give anti‐carbopalladation products. Prerequisite is the exclusion of other reaction pathways to provoke the cis–trans isomerization of the syn‐carbopalladation intermediate. Detailed mechanistic studies of this crucial step by experimental and computational means were performed. Application of an intramolecular version for the synthesis of oligocyclic compounds and substituted dibenzofurans is also described.