Borylative Radical Cyclizations of Benzo[3,4]cyclodec‐3‐ene‐1,5‐diynes and N‐Heterocyclic Carbene‐Boranes | Zendy

Watanabe Takashi | Zendy; Hirose Daisuke | Zendy; Curran Dennis P. | Zendy; Taniguchi Tsuyoshi | Zendy

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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.

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