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. Author manuscript; available in PMC: 2015 Jul 6.
Published in final edited form as: J Am Chem Soc. 2013 Nov 11;135(46):17238–17241. doi: 10.1021/ja406654y

Table 5.

Relative Rates of Aziridination and C–H Insertion

graphic file with name nihms702492u8.jpg
entry R1-R3 catalyst (AgOTf, phen) product(s) init rate (mmol/min*mL)a
1 Me, Me, Me
19 		20 mol%, 25 mol% 20 1.8×10−3 (98% yield)
2 10 mol%, 30 mol% 20 no reaction
3 20 mol%, 25 mol%, 20 mol% BHT 20 1.4×10−3 (48% yield)
4 Me, Me, H
3a 		20 mol%, 25 mol% 4a 1.3×10−3
5 20 mol%, 25 mol%, 20 mol% BHT 5a 9.6×10−4
6 20 mol%, 60 mol% 5a 2.8×10−4
7 20 mol%, 60 mol%, 20 mol% BHT 5a 2.1×10−4
8 C5H11, H, Me
21 		20 mol%, 25 mol% 22 9.85×10−4 (88% yield)
9 20 mol%, 60 mol% 22 36% yieldb
10 20 mol%, 25 mol%, 20 mol% BHT 22 6.15×10−4
11 C5H11, H, H
3d 		20 mol%, 25 mol% 4d 5.73×10−4
12 20 mol%, 25 mol%, 20 mol% BHTc 4d (26%)
5d (34%)		 3.31×10−4
2.31×10−4
13 20 mol%, 60 mol% 5d 1.58×10−4
14 20 mol%, 60 mol%, 20 mol% BHT 5d 2.94×10−4
a

The rate of product formation was monitored by 1H NMR using mesitylene as the internal standards. The indicated initial rates are the average of the three runs, and the standard deviations are included in the SI.

b

Yield after 21 h, 73% conversion.

c

The ratio of 4d:5d was 1:1.