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Synthesis and Properties of Sila[n]helicenes via Dehydrogenative Silylation of C–H Bonds under Rhodium Catalysis
Author(s) -
Masahito Murai,
Ryo Okada,
Atsushi Nishiyama,
Kazuhiko Takai
Publication year - 2016
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.6b02134
Subject(s) - helicene , chemistry , rhodium , silylation , enantiomer , catalysis , ring (chemistry) , benzene , ligand (biochemistry) , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , molecule , receptor , biochemistry
Use of a rhodium catalyst with (R)-(S)-BPPFA ligand allows efficient synthesis of sila[n]helicenes via dehydrogenative silylation of C-H bonds. By selecting the proper ligands, the current method provides the ability to prepare unsymmetrical sila[n]helicene derivatives without any oxidants. The resulting sila[6]helicene is a rare example of a five-membered ring-fused [6]helicene, which was isolated as a single pure enantiomer without substituents on the terminal benzene rings.

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