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Hydroaminoalkylation of Allylsilanes and a One‐Pot Procedure for the Synthesis of 1,5‐Benzoazasilepines
Author(s) -
Lühning Lars H.,
Strehl Julia,
Schmidtmann Marc,
Doye Sven
Publication year - 2017
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.201605923
Subject(s) - regioselectivity , amination , chemistry , silane , alkene , titanium , catalysis , intermolecular force , one pot synthesis , organic chemistry , silicon , combinatorial chemistry , molecule
Allylsilanes undergo highly regioselective intermolecular alkene hydroaminoalkylation with secondary amines in the presence of a titanium mono(formamidinate) catalyst. Corresponding reactions of a suitable allyl(2‐bromophenyl)silane which exclusively deliver the branched hydroaminoalkylation products combined with a subsequent Buchwald–Hartwig amination result in the development of an elegant one‐pot procedure for the synthesis of literature‐unknown silicon analogues of 1,5‐benzodiazepines, the so‐called 1,5‐benzoazasilepines.