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. 2016 Nov 4;18(21):5449-5451.
doi: 10.1021/acs.orglett.6b02722. Epub 2016 Oct 18.

Palladium-Catalyzed Aerobic Intramolecular Aminoacetoxylation of Alkenes Enabled by Catalytic Nitrate

Jiaming Li  1 , Robert H Grubbs  1 , Brian M Stoltz  1
Affiliations

Palladium-Catalyzed Aerobic Intramolecular Aminoacetoxylation of Alkenes Enabled by Catalytic Nitrate

Jiaming Li et al. Org Lett. .

Abstract

A mild aerobic intramolecular aminoacetoxylation method for the synthesis of pyrrolidine and indoline derivatives was achieved using molecular oxygen as the oxidant. A catalytic NOx species acts as an electron transfer mediator to access a high-valent palladium intermediate as the presumed active oxidant.

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Conflict of interest statement

Notes

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Proposed Catalytic Cycle. The full ligand set on palladium is not shown for clarity. Intermediate (II) could be a different high-valent palladium species such as PdIII.
Scheme 1
Scheme 1
Aminopalladation and Subsequent Transformations
Scheme 2
Scheme 2
Pd-catalyzed Aerobic Methods Enabled by NOx Species
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