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π‐Helicenes Truncated to a Minimum: Access Through a Domino Approach Involving Multiple Carbopalladations and a Stille Coupling
Author(s) -
Milde Bastian,
Leibeling Markus,
Pawliczek Martin,
Grunenberg Jörg,
Jones Peter G.,
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.201408637
Subject(s) - stille reaction , domino , coupling (piping) , computer science , mathematics , chemistry , materials science , organic chemistry , composite material , polymer , catalysis
A novel type of π‐helicenes is reported, in which the π‐system is truncated to an all‐s‐ cis all‐ Z oligoene chain. A domino sequence was developed, consisting of up to four consecutive carbopalladation reactions and a terminal Stille cross‐coupling, to generate these entities in one step from the respective linear oligoynes. Despite the minimal π‐system, very high optical rotation values were encountered for the single enantiomers. X‐ray crystallography confirmed their screw‐shaped structure.