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. Author manuscript; available in PMC: 2019 Jun 18.

Published in final edited form as: J Am Chem Soc. 2018 Nov 15;140(47):16020–16025. doi: 10.1021/jacs.8b09156

Table 2.

Optimization of reactions



Entry	Modifications	Yield of 3a(%)^a	3a:3a’^d	Time (h)
1	none	31/62	1.6:1	5/17
2	no cataylst or in dark	0	na	17^b
3	without amine	0	na	17^b
4	−10 °C instead of 0°C	29/64	1.7:1	5/25
5	DIPEA (1.0 equiv)	25/57	2:1	5/23^b
6	DIPEA (1.8 equiv)	36/64	1.9:1	5/18
7	DIPEA (2.5 equiv)	38/57	1.3:1	5/15
8	0.25 mol% catalyst, DIPEA (1.8 equiv)	31/58	1.8:1	5/24
9	0.025 mol% catalyst, DIPEA (1.8 equiv)	6/28	1.6:1	5/24^b
10	H₂O (10 equiv), DIPEA (1.8 equiv)	57/65	1.9:1	3/4
11	H₂O (15 equiv), DIPEA (1.8 equiv)	59/65	1.9:1	3/4
12	Entry 10 with 0.4 equiv TEMPO	39/68	2.1:1	4/10

^a determined by ¹⁹F NMR analysis. Reaction complete unless otherwise noted.

^bReaction did not go to completion over extended time, observed 0%, 0%, 83% and 44% conversion of 1 in entries 2, 3, 5 and 9 respectively.

^dReported for the final time point.