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Borylative Radical Cyclizations of Benzo[3,4]cyclodec‐3‐ene‐1,5‐diynes and N‐Heterocyclic Carbene‐Boranes
Author(s) -
Watanabe Takashi,
Hirose Daisuke,
Curran Dennis P.,
Taniguchi Tsuyoshi
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.201700689
Subject(s) - boranes , radical , carbene , chemistry , medicinal chemistry , radical cyclization , photochemistry , organic chemistry , catalysis , boron
Borylative radical cyclization of benzo[3,4]cyclodec‐3‐ene‐1,5‐diynes to provide 5‐borylated 6,7,8,9‐tetrahydrobenzo[ a ]azulenes has been developed. The experimental results suggest that the reaction proceeds by a radical chain mechanism, in which di‐ tert ‐butyl hyponitrite (TBHN) works as a good radical initiator to form boryl radicals from N‐heterocyclic carbene–boranes (NHC‐boranes). The present reaction is a rare model that illustrates addition of boryl radicals to alkynes.