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. 2014 Sep 15;356(13):2831-2837.
doi: 10.1002/adsc.201400742.

Intermolecular [3+2] Annulation of Cyclopropylanilines with Alkynes, Enynes, and Diynes via Visible Light Photocatalysis

Theresa H Nguyen  1 , Scott A Morris  1 , Nan Zheng  1
Affiliations

Intermolecular [3+2] Annulation of Cyclopropylanilines with Alkynes, Enynes, and Diynes via Visible Light Photocatalysis

Theresa H Nguyen et al. Adv Synth Catal. .

Abstract

One-step synthesis of carbocycles substituted with amines from simple starting materials remains rare. We recently developed intermolecular [3+2] annulation of cyclopropylanilines with alkenes and alkynes that enable this one-step synthesis. Herein, we report our findings for a fullscale study of the annulation. Significant expansion of the substrate scope for both cyclopropylanilines and alkynes is achieved. A range of structurally diverse carbocycles substituted with amines is prepared.

Keywords: [3+2] annulation; alkynes; cyclopropylanilines; diynes; enynes; intermolecular; photocatalysis; visible light.

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Figures

Figure 1
Figure 1
Rationale for observed selectivity using DFT calculations.
Scheme 1
Scheme 1
Proposed intermediate distonic ion in the [3+2] annulations.
Scheme 2
Scheme 2
Removal of para-methoxyphenyl (PMP) group.
See this image and copyright information in PMC

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