“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.

Figure 1. Generic reaction scheme for the alkylation of an amine.In order to probe the mechanism and optimize the conditions for catalysis, a student modified the procedure and investigated several different reaction conditions. The student’s results can be summarized in the table below:

 

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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