Tasker Sarah Z, Jamison Timothy F
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
J Am Chem Soc. 2015 Aug 5;137(30):9531-4. doi: 10.1021/jacs.5b05597. Epub 2015 Jul 21.
Nickel/photoredox catalysis is used to synthesize indolines in one step from iodoacetanilides and alkenes. Very high regioselectivity for 3-substituted indoline products is obtained for both aliphatic and styrenyl olefins. Mechanistic investigations indicate that oxidation to Ni(III) is necessary to perform the difficult C-N bond-forming reductive elimination, producing a Ni(I) complex, which in turn is reduced to Ni(0). This process serves to further demonstrate the utility of photoredox catalysts as controlled single electron transfer agents in multioxidation state nickel catalysis.
镍/光氧化还原催化用于从碘代乙酰苯胺和烯烃一步合成吲哚啉。对于脂肪族烯烃和苯乙烯基烯烃，均可获得对3-取代吲哚啉产物非常高的区域选择性。机理研究表明，氧化为Ni(III)对于进行困难的C-N键形成还原消除反应是必要的，该反应生成Ni(I)配合物，而Ni(I)配合物又被还原为Ni(0)。该过程进一步证明了光氧化还原催化剂作为多氧化态镍催化中可控单电子转移试剂的实用性。
