P650
“Because a wide array of important compounds (such as natural products, pharmaceuticals, and functional polymers/materials) contain nitrogen, the development of methods for the efficient formation of C−N bonds is a central challenge in organic chemistry. The formation of a Csp3−N bond through a substitution reaction (SN2) between a nitrogen nucleophile and an alkyl halide is a classic method that is widely used, despite its limitations.
A laboratory discovers that the use of a preliminary Copper Iodide (CuI) catalyst, in coordination with a specific wavelength of light, could successfully alkylate terminal amine groups in good yields.
![](https://member.mytestingsolution.com/wp-content/uploads/2019/04/QbankP139.gif)
Figure 1. Generic reaction scheme for the alkylation of an amine.
Table 1. Modification of reaction conditions.
Entry | Conditions | Yield |
1 | 10% CuI, 254 nm hv | 90% |
2 | No CuI | <2% |
3 | No hv | <2% |
4 | CuBr, instead of CuI | 82% |
5 | CuCl, instead of CuI | 78% |
6 | hv (300 nm) | 10% |
7 | hv (100 W Hg lamp) | <2% |
8 | 0 °C | 33% |
9 | 5.0% CuI | 87% |
10 | 2.5% CuI | 83% |
11 | 1.0% CuI | 69% |
12 | 0.5% CuI | 30% |
”
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