Divergent synthesis of 3,4-dihydrodibenzo[b,d]furan-1(2H)-ones and isocoumarins via additive-controlled chemoselective C-C or C-N bond cleavage

作者：Zuo, Youpeng; He, Xinwei; Ning, Yi; Zhang, Lanlan; Wu, Yuhao; Shang, Yongjia^*

来源：New Journal of Chemistry, 2018, 42(3): 1673-1681.

DOI：10.1039/c7nj03799f

• ALPHA-DIAZOCARBONYL COMPOUNDS
• DIAZO-COMPOUNDS
• H ACTIVATION
• CYCLIC 2-DIAZO-1,3-DIKETONES
• REGIOSELECTIVE SYNTHESIS
• OXIDATIVE CYCLIZATION
• SELECTIVE SYNTHESIS
• ALKYNES
• ANNULATION
• DIBENZOFURANS

Rh(III)-Catalyzed C-C/C-O bond formation between cyclic 2-diazo-1,3-diketones and salicylamides with additive-controlled chemoselectivity is described. The reaction proceeded under mild reaction conditions and exhibited good functional group tolerance and scalability. 3,4-Dihydrodibenzo[b, d]furan-1(2H)-ones were obtained in moderate to excellent yields (55-90%) through a tandem N-H activation/C-C cleavage/etherification process when AgNTf2 was used as the additive, whereas utilizing Cu(OAc)(2) afforded isocoumarins in good yields (60-86%) via a C-H activation/C-N cleavage/lactonization pathway.

• 出版日期2018-2-7
• 单位安徽师范大学