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Nickel/Photo-Cocatalyzed Regioselective Ring Opening of N-Tosyl Styrenyl Aziridines with Aldehydes
Organic Letters ( IF 4.9 ) Pub Date : 2021-09-20 , DOI: 10.1021/acs.orglett.1c02514 Pei Fan 1, 2 , Youxiang Jin 2 , Jiawei Liu 2 , Rui Wang 2 , Chuan Wang 2
Organic Letters ( IF 4.9 ) Pub Date : 2021-09-20 , DOI: 10.1021/acs.orglett.1c02514 Pei Fan 1, 2 , Youxiang Jin 2 , Jiawei Liu 2 , Rui Wang 2 , Chuan Wang 2
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Aldehydes and aziridines are both intrinsic electrophilic reagents, and thus the coupling reaction between these two compounds is highly challenging. In this protocol, the merger of nickel and hydrogen-atom-transfer photocatalysis successfully enables the ring opening of N-tosyl styrenyl aziridines with aldehydes, providing a novel and atom-economical access to a variety of β-amino ketones with complete regiocontrol. The preliminary mechanistic studies reveal that the ring opening reaction proceeds with a cooperative catalytic mode: aldehydes are converted into acyl radicals by tetrabutylammonium decatungstate under irradiation, whereas the nickel catalyst is engaged in the ring opening of aziridines and the following carbon–carbon bond-forming step.
中文翻译：
N-甲苯磺酰基苯乙烯基氮丙啶与醛的镍/光共催化区域选择性开环
醛和氮丙啶都是固有的亲电试剂，因此这两种化合物之间的偶联反应极具挑战性。在该协议中，镍和氢原子转移光催化的合并成功地使N-甲苯磺酰基苯乙烯基氮丙啶与醛开环，为获得具有完全区域控制的各种 β-氨基酮提供了一种新颖且原子经济的途径。初步机理研究表明，开环反应以协同催化模式进行：醛在辐照下被四丁基十钨酸铵转化为酰基，而镍催化剂参与氮丙啶的开环和以下碳-碳键的形成步。
更新日期：2021-10-01
中文翻译：
N-甲苯磺酰基苯乙烯基氮丙啶与醛的镍/光共催化区域选择性开环
醛和氮丙啶都是固有的亲电试剂，因此这两种化合物之间的偶联反应极具挑战性。在该协议中，镍和氢原子转移光催化的合并成功地使N-甲苯磺酰基苯乙烯基氮丙啶与醛开环，为获得具有完全区域控制的各种 β-氨基酮提供了一种新颖且原子经济的途径。初步机理研究表明，开环反应以协同催化模式进行：醛在辐照下被四丁基十钨酸铵转化为酰基，而镍催化剂参与氮丙啶的开环和以下碳-碳键的形成步。
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