Table 1.

Reaction optimization.

Entry	Variation from standard conditionsa	% Yieldb
1	none	46
2	Pt (+) | C (–) instead of Pt (+) | Pt (–)	≪25c
3	C (+) | Pt (–) instead of Pt (+) | Pt (–)	40
4	DMSO as solventd	<22
5	MeOH as solventd	n.d.e
6	Bu4NCl instead of Bu4NBrd	35
7	Bu4NI instead of Bu4NBrd	<21
8	Bu4NBF4 instead of Bu4NBrd	44
9	0.8 equiv Bu4NBr instead of 2.4 equiv Bu4NBrd	40
10	4.0 equiv Bu4NBr instead of 2.4 equiv Bu4NBrd	43
11	0 °C instead of rt	45
12	60 °C instead of rt	<44
13	20 mA instead of 12 mA, 1.0 F/mol	<33
14	6 mA instead of 12 mA, 1.0 F/mol	46
15	no electric current	n.d.c,e

^aStandard conditions: 1 (0.5 mmol), 0.3 M Bu₄NBr in DMF (4.0 mL × 2), divided cell, 12 mA, rt, 1.0 F/mol of electricity against 0.5 mmol of substrate 1. ^bIsolated yields using preparative GPC separation of the crude materials. ^cObserved from gas chromatography (GC) analysis. ^dIn both anodic and cathodic chambers. ^en.d. = no detection.