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. Author manuscript; available in PMC: 2021 Jan 7.
Published in final edited form as: J Am Chem Soc. 2017 Feb 3;139(6):2132–2135. doi: 10.1021/jacs.6b09203

Table 1.

Summary of Optimization Studies for Dichlorination

graphic file with name nihms-1657760-t0002.jpg
entry solvent Temp XCI (equiv) Yielda 5a:6a:7a:8a er (5a)b
1 MeCN 23 TEAC (15) 82 55:0:45:0 50:50
2 MeCN 23 NaCl (15) 70 0:0:13:87 nd
3 MeCN 23 LiCl (15) 78 79:0:21:0 80:20
4 MeCN −30 LiCl (15) 84 95:0:5:0 92:8
5 TFE 23 LiCl (15) 82 45:56:0:0 97:3
6 TFE −30 LiCl (50) 86 86:14:0:0 98:2
7 TFE −30 LiCl (100) 95 95:5:0:0 98:2
8 TFE 23 LiCl (100) 90 95:5:0:0 92:8
9 TFE 23 TEAC (100) 84 66:34:0:0 93:7
10 TFE 23 NaCl (100) 82 0:89:11:0 nd
11 TFE 23 CsCl (100) 87 55:44:3:0 95:5
12C TFE 23 Cl2 (gas) 83 16:43:41:0 50:50
a

Combined yield, determined by NMR.

b

Determined by chiral HPLC.

c

Cl2 gas was generated in situ and bubbled into the reaction; DCDMH = dichlorodimethyl hydantoin; TFE = 2,2,2-trifluoroethanol; TEAC = tetraethylammonium chloride.