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17729-59-8

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Selective ortho C?H Cyanoalkylation of (Diacetoxyiodo)arenes through [3,3]-Sigmatropic Rearrangement
We herein report a robust catalyst-free cross-coupling between ArI(OAc)2 and α-stannyl nitriles, aided by TMSOTf. The transformation introduces a cyanoalkyl group to the ortho position of ArI(OAc)2 and simultaneously reduces the aryl iodine(III) to iodide, thus providing α-(2-iodoaryl) nitrile as the product. This transformation could be completed within 5 min at ?78 °C and features superb functional-group tolerance and efficient scalability. DFT calculations indicate that the formation of a ketenimine(aryl)iodonium intermediate and subsequent [3,3]-sigmatropic rearrangement are involved as key steps.
Tian, Junsong,Luo, Fan,Zhang, Chaoshen,Huang, Xin,Zhang, Yage,Zhang, Lei,Kong, Lichun,Hu, Xiaochun,Wang, Zhi-Xiang,Peng, Bo
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p. 9078 - 9082
(2018/07/25)

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Chemical Properties

Boiling Point: 140-144 °C(Press: 1.3 Torr)
Refractive Index: 1.4860 (20℃)
PSA: 0.00000
LogP: 3.58780

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