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Development of New Radical‐mediated Selective Reactions Promoted by Hypervalent Iodine(III) Reagents
The Chemical Record ( IF 6.6 ) Pub Date : 2020-11-19 , DOI: 10.1002/tcr.202000132
Akira Matsumoto 1 , Hyo‐Jun Lee 2 , Keiji Maruoka 1, 3
Affiliation  

In this account, we describe our recent developments on the four‐types of hypervalent iodine(III)‐mediated radical reactions in organic synthesis. Firstly, the activation of aldehydic C−H bonds can be successfully effected with hypervalent iodine(III) reagents, thereby allowing the synthesis of various ketones with high efficiency. Secondly, the site‐selective oxidation of unactivated C(sp3)−H bonds of hydrocarbon substrates was realized with designer hypervalent iodine(III) reagents. Thirdly, various perfluoroalkyl and α‐aminoalkyl radicals can be generated from sodium perfluoroalkanesulfinates and sodium α‐aminoalkanesulfinates, respectively, under the influence of hypervalent iodine(III) reagents. Finally, the efficient generation of difluoromethyl radical from hypervalent difluoroacetoxyliodine(III) reagent was realized by photolysis. These four different strategies are illustrated by using various selective radical approaches.

中文翻译:

高价碘试剂促进的新的自由基介导的选择性反应的发展

因此,我们描述了有机合成中高价碘(III)介导的四种自由基反应的最新进展。首先,醛键CH键的活化可以通过高价碘(III)试剂成功实现,从而可以高效合成各种酮。其次,未活化C(sp 3的位点选择性氧化碳氢化合物底物的)-H键通过设计者高价碘(III)试剂实现。第三,在高价碘(III)试剂的影响下,全氟烷烃亚磺酸钠和α-氨基烷烃亚磺酸钠可分别产生各种全氟烷基和α-氨基烷基。最后,通过光解实现了由高价二氟乙酰氧基碘(III)试剂高效生成二氟甲基自由基。通过使用各种选择性的基本方法来说明这四种不同的策略。
更新日期:2020-11-19
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