Citation: Yan Xin ZHU, Yuan Hua WANG, Zhi Yong CHEN, Wen Hao HU. Unexpected Side Reaction in the Intermolecular N-H Insertion of Phenyl Diazoacetates with Arylamines[J]. Chinese Chemical Letters, ;2005, 16(3): 307-310. shu

Unexpected Side Reaction in the Intermolecular N-H Insertion of Phenyl Diazoacetates with Arylamines

Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041

Received Date: 9 February 2004

Fund Project: We are grateful for financial support from the Chinese Academy of Sciences and National Nature Science Foundation of China (20202011). We thank Prof. Kaibai Yu of Chengdu Institue of Organic Chemistry for X-ray measurement.

Unexpected side reaction is discovered from the N-H insertion of phenyl diazoacetates with arylamines in the presence of Rh₂(OAc)₄ catalyst. This side reaction is not evident with copper catalysts such as Cu (acac)₂ or Cu (OTf)₂. Good yieldof the N-H insertion was obtained by using 0.2% of copper catalyst.
- N-H insertion,
- diazoester,
- carbene,
- ylide,
- rearrangement.
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14. [14]
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