Cobalt-Catalyzed N−O and C−C Bonds Cleavage in 1,2-Oxazetidines: Solvent-Controlled C−H Aminomethylation and Hydroxymethylation ofHeteroarenes

Song Li,^aPengfei Shi,^aRui-Hua Liu,^aXu-Hong Hu,*,^aand Teck-Peng Loh*^,a,b

^aInstitute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing Tech University, Nanjing 211816, China

^bDivision of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore

Abstract:An efficient cobalt-catalyzed ring-opening reaction of bench-stable 1,2-oxazetidines with heteroarenes was unprecedentedly developed.The sustainableCp*Co(III)catalyst enables a distinctive merger of C−H activation with a concomitant N−O and C−C cleavages of 1,2-oxazetidine,leading to site-selective C−H aminomethylation and hydroxymethylation of heteroaromatic compounds containing a broad range of functional groups.Preliminary control experiments unravel some essential mechanistic features ofthis one-pot transformation.

Org. Lett.2019,21, 1602−1606(2017年影响因子：6.492).

论文链接：https://pubs.acs.org.ccindex.cn/doi/10.1021/acs.orglett.9b00141