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Palladium‐Catalyzed Difunctionalization of 1,3‐Diene with Amine and Disilane under a Mild Re‐oxidation System
Author(s) -
Torii Kazuyuki,
Kawakubo Atsushi,
Lin Xianjin,
Fujihara Tetsuaki,
Yajima Tatsuo,
Obora Yasushi
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202100043
Subject(s) - disilane , allylic rearrangement , chemistry , amine gas treating , diene , regioselectivity , moiety , palladium , ligand (biochemistry) , yield (engineering) , stereoselectivity , catalysis , silanes , medicinal chemistry , combinatorial chemistry , organic chemistry , silane , materials science , biochemistry , natural rubber , receptor , metallurgy
A highly regioselective and stereoselective difunctionalization reaction of 1,3‐diene with amine and disilane to form C−N and C−Si bonds via a one‐step Pd/Cu/O 2 system is disclosed. The difunctionalization reaction affords allylic silanes, including the allylic amine moiety, in up to 92 % yield in the absence of any acid, base, or external ligand. The developed synthetic methodology can be scaled to 100 g in high yield with high Z ‐selectivity, which demonstrates the feasibility of the reaction for industrial applications.