Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2020, Issue 8, Pages 909-916Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201901562
Keywords
C-H amination; Asymmetric reaction; Catalytic reaction; Engineered enzyme; C-H functionalization
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Funding
- JSPS KAKENHI [JP18H04264]
- International Institute for Carbon-Neutral Energy Research (WPI-I2CNER) from MEXT, Japan
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C-H bonds are ubiquitous and abundant in organic molecules. If C-H bonds could be directly converted to desired functional groups in a chemo-, site-, and stereoselective manner, C-H functionalization would be a strong and useful tool for organic synthesis. Recent developments in catalytic and enzymatic chemistry have achieved highly sustainable and selective nitrene C-H insertion. Initially, C-H amination was inspired by model studies on enzymatic oxidation and used iminoiodinanes, nitrogen analogs of iodosobenzene, as nitrene precursors. Transition-metal/iminoiodinane systems are well studied and established. These systems can directly introduce sulfonamide groups with excellent stereoselectivity, albeit with co-production of iodobenzene as waste material. Fortunately, the atom economics of this methodology were improved by introducing highly sustainable nitrene sources such as azide compounds and 1,2,4-dioxazol-5-one derivatives. In this review, we present the details of these developments with respect to their catalysts and nitrene sources.
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