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Metal‐Carbene‐Templated Photochemistry in Solution: A Universal Route towards Cyclobutane Derivatives
Author(s) -
Li Yang,
Jin GuangFeng,
An YuanYuan,
Das Rajorshi,
Han YingFeng
Publication year - 2019
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201900348
Subject(s) - cyclobutane , chemistry , carbene , metal , pyridine , medicinal chemistry , stereochemistry , photochemistry , ring (chemistry) , catalysis , organic chemistry
Summary of main observation and conclusion A series of dicarbene‐bridged metallacycles [Ag 2 ( 1 ) 2 ](PF 6 ) 2 , [Ag 2 ( 2 ) 2 ](BF 4 ) 2 , [Ag 2 ( 3 ) 2 ](PF 6 ) 2 , [Ag 2 ( 7 ) 2 ](BF 4 ) 2 , [Ag 2 ( 8 ) 2 ](BF 4 ) 2 and [Ag 2 ( 11 ) 2 ](PF 6 ) 2 were obtained in high yields via the reactions of 1,2,4‐triazole‐, 1,2,3‐triazole‐ and imidazo[1,5‐ a ]pyridine‐based ligands with Ag 2 O in CH 3 CN. The C=C double bonds in all of the newly synthesized metallacycles went through [2 + 2] photodimerization under UV irradiation condition ( λ = 365 nm, T = 298 K) yielding the dinuclear rctt ‐cyclobutane‐silver(I) complexes [Ag 2 ( 4 )](PF 6 ) 2 , [Ag 2 ( 5 )](BF 4 ) 2 , [Ag 2 ( 6 )](PF 6 ) 2 , [Ag 2 ( 9 )](BF 4 ) 2 , [Ag 2 ( 10 )](BF 4 ) 2 and [Ag 2 ( 12 )](PF 6 ) 2 , respectively with quantitative yields. Treatment of the these cyclobutane‐bridged silver(I) complexes with NH 4 Cl resulted in the exclusive formation of cyclobutane derivatives after removal of the silver(I) metal ions.