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. Author manuscript; available in PMC: 2022 Jan 24.
Published in final edited form as: Org Lett. 2021 Feb 15;23(5):1588–1593. doi: 10.1021/acs.orglett.0c04305

Table 1.

Initial Optimizations.

entry Eq.
NaBH4
Solvent Time
(hours)
% NMR
Yield
% Conversion
MPFBb
1 0.50 MeOH 10 0 ~100
2 0.50 EtOH 10 6 72
3 a 0.50 THF 10 <2 <2
4 a 0.50 DME 10 46 46
5 0.50 DMF 10 70 72
6 0.50 DMSO 10 97 98
7 0.33 DMSO 2 23 23
8 0.66 DMSO 2 43 43
9 1.00 DMSO 2 99 99
10 2.00 DMSO 2 99 99
a

Reactions were run as suspensions.

b

Determined using 19F NMR.