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. Author manuscript; available in PMC: 2019 Jun 20.
Published in final edited form as: J Org Chem. 2017 Dec 5;82(24):13500–13516. doi: 10.1021/acs.joc.7b02623

Table 3.

Photoredox Catalyzed Cyclization of α-Bromo β-Keto Ester 58

graphic file with name nihms-1031082-t0050.jpg
Entry Solvent Catalyst (equiv.) Base (equiv.) Time Yield 8a
1 CH2G2 (0.1M) fac-Ir(ppy)3 (0.5 mol%) DABCO (2.0) 1.5h 7%
2 CH2G2 (0.05M) fac-Ir(ppy)3 (0.5 mol%) DABCO (2.0) 1.5h 8%
3 CH2Cl2 (0.02M) fac-Ir(ppy)3 (0.5 mol%) DABCO (2.0) 1.5h 14%
4 MeCN (0.02M) fac-Ir(ppy)3 (0.5 mol%) DABCO (2.0) 3.5h 13%
5 MeCN (0.02M) Ir(ppy)2(dtbpy)PF6 (1.0 mol%) DABCO (2.0) 0.5h 10%
6 MeCN (0.02M) Ir(dF-ppy)3 (1.0 mol%) DABCO (2.0) 0.5h 8%
7 MeCN (0.02M) Ir(dF-ppy)2(dtbpy)PF6 (1.0 mol%) DABCO (2.0) 0.5h 10%
8 MeCN (0.02M) Ru(bpy)3(PF6)2 (1.0 mol%) DABCO (2.0) 0.5h 13%
9 MeCN (0.02M) Ru(bpy)3(PF6)2 (0.5 mol%) DABCO (2.0) 0.5h 12%
10 MeCN (0.02M) Ru(bpy)3(PF6)2 (0.1 mol%) DABCO (2.0) 0.5h 11%
11 MeCN (0.02M) Ru(bpy)3(PF6)2 (0.01 mol%) DABCO (2.0) 0.5h 10%

Std. conditions: Room temperature, blue LEDs. Yield determined by internal standard (0.02M 1,3,5-trimethoxybenzene in CDCI3).