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. Author manuscript; available in PMC: 2014 Apr 24.
Published in final edited form as: Angew Chem Int Ed Engl. 2010 Oct 18;49(43):8004–8007. doi: 10.1002/anie.201003924

Table 1.

Anodic coupling of amines and dithioketene acetals.

graphic file with name nihms-411625-t0006.jpg

Entry Subst. n R1,R2,R3 Ep/2[a]
[V]
Yield[b]
[%]
1 4a 1 R1 = Me
R2 = R3 = H
0.60 84
2 4b 1 R1 = R2 = Me
R3 = H
0.62 81
(>20:1)
3 4c 1 R1 = R3 = Me
R2 = H
0.58 92[c]
(3:2)
4 4d 1 R1 = CH=CHMe
R2 = Me, R3 = H
-- 90
(10:1)
5 4e 2 R1 = Me
R2 = R3 = H
0.65 72
6 4f 2 R1 = R2 = Me
R3 = H
0.68 83[d]
(10:1)
7 4g 2 R1 = R3 = Me
R2 = H
0.67 64[e]
(2:1)
8 4h 3 R1 = Me
R2 = R3 = H
0.70 --
[a]

Measured vs. Ag/AgCl on a carbon anode in acetonitrile.

[b]

Ratio in parenthesis is diastereomeric ratio.

[c]

A 40% yield (measured by 1H NMR using an internal standard) of product was obtained when 6 eq. of 2,6-lutidine was used as the base instead of LiOMe.

[d]

2.3 F/mol.

[e]

2.4 F/mol.