DDQ-Mediated Oxidative Radical Cycloisomerization of 1,5-Diynols: Regioselective Synthesis of Benzo[b]fluorenones under Metal-Free Conditions

作者：Zhu, Hui; Chen, Zhiyuan^*

来源：Organic Letters, 2016, 18(3): 488-491.

DOI：10.1021/acs.orglett.5b03533

• 4+2 CYCLOADDITION REACTIONS
• ELECTROPHILIC CYCLIZATION
• KINAMYCIN BIOSYNTHESIS
• REARRANGEMENT
• DERIVATIVES
• DIARYLACETYLENES
• ARYL

A regio- and chemoselective oxidative cycloisomerization reaction of acyclic 1,5-diynols has been developed. The reaction proceeds under metal-free reaction conditions with high efficiency and broad functional group tolerance, which offers a general and straightforward access to benzo[b]fluorenones under metal-free conditions. The preliminary mechanistic studies revealed the possible involvement of a Meyer-Schuster rearrangement combined with an oxidative radical cyclization.

• 出版日期2016-2-5
• 单位江西师范大学