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. Author manuscript; available in PMC: 2020 Mar 18.
Published in final edited form as: Angew Chem Int Ed Engl. 2019 Feb 15;58(12):4002–4006. doi: 10.1002/anie.201812227

Table 1.

Reaction Optimization

graphic file with name nihms-1014655-t0006.jpg
entry PG Photocatalyst R Base Yield(%)b
1 Tf A Bn CS2CO3 50
2 Tf A Bn K2CO3 54
3 Tf A Bn K3PO4 58
4 Tf B Bn K3PO4 65
5 Tf A tBu quinuclidine 71
6 Tf B tBu quinuclidine 77 c
7 COCF3 B tBu quinuclidine 0
g Ts B tBu quinuclidine 0
9 Ac B tBu quinuclidine 0
graphic file with name nihms-1014655-t0007.jpg

[a]1a (0.1 mmol), alkene (0.15 or 0.3 mmol), base (0.2 mmol), photocatalyst (2.0 mol%), DMF (0.2M), 34 W blue LED, ~ 40 °C, 16h.

[b]Yields determined by 1H NMR using trimethoxybenzene as an internal standard.

[c]Yield of isolated product.

[d]PG = protecting group; Tf = triflyl; Ts = tosyl; Ac = acetyl; DMF = dimethylformamide; Bn = benzyl; tBu = tert-butyl; Et = ethyl; Me = methyl.