Reaction optimization of reductive amidation.

Entry	Variation from standard conditionsa	Yieldb (%)
1	None	81 (78)c
2	TMS3Si–H instead of CH3(OCH3)2Si–H	60
3	Eosin Y instead of TBADT	<2
4	Without CF3COOH	40
5	CH3COOH instead of CF3COOH	41
6	60 °C instead of 30 °C	58
7	Without TBADT	6
8	Without light irradiation	0

^aStandard conditions: 1a (0.1 mmol), 2a (3 equiv.), TBADT (2 mol%), CF₃COOH (30 mol%), H–Si(OCH₃)₂CH₃ (2.5 equiv.), CH₃CN (2 mL), 2 × 40 W LEDs (390 nm), 30 °C, 24 h.

^bYields are based on the analysis of the ¹H NMR spectra of the crude product mixture using CH₂Br₂ as an internal standard.

^cIsolated yields.