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. 2014 Apr 29:10:975-80.
doi: 10.3762/bjoc.10.96. eCollection 2014.

Visible light mediated intermolecular [3 + 2] annulation of cyclopropylanilines with alkynes

Theresa H Nguyen  1 , Soumitra Maity  1 , Nan Zheng  1
Affiliations

Visible light mediated intermolecular [3 + 2] annulation of cyclopropylanilines with alkynes

Theresa H Nguyen et al. Beilstein J Org Chem. .

Abstract

Intermolecular [3 + 2] annulation of cyclopropylanilines with alkynes is realized using visible light photoredox catalysis, yielding a variety of cyclic allylic amines in fair to good yields. This method exhibits significant group tolerance particularly with heterocycles. It can also be used to prepare complex heterocycles such as fused indolines.

Keywords: [3 + 2]; alkyne; annulation; cyclopropylaniline; photoredox catalysis; visible light.

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Figures

Figure 1
Figure 1
Substrate scope.
Scheme 1
Scheme 1
Synthesis of a fused indoline.
Scheme 2
Scheme 2
Proposed catalytic cycle.
See this image and copyright information in PMC

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