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. 2014 Oct 30;6(2):987–992. doi: 10.1039/c4sc02365j

Table 1. Optimization of the reaction conditions.

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Inline graphic
Entry Cat a Additive b Solvent Conv. [%] Yield c
1 A DMSO (0.34 M) ∼35% d
2 A (BnO)2P(O)OH DMSO (0.34 M) 100 10 a %
3 A (BnO)2P(O)OH DMSO (0.34 M) 100 30%
4 A Benzoic acid DMSO (0.34 M) 100 8%
5 A Acetic acid DMSO (0.34 M) 100 10%
6 A PTSA DMSO (0.34 M) 100 0%
7 A H3PO4 DMSO (0.34 M) 100 40%
8 B H3PO4 DMSO (0.34 M) 60
9 C H3PO4 DMSO (0.34 M) 75
10 A H3PO4 DMF (0.34 M) 60
11 A H3PO4 ACN (0.34 M) 20
12 A H3PO4 DMSO (0.09 M) 100 65 e %
13 A H3PO4 DMSO (0.09 M) 100 51 f %
14 A H3PO4 DMSO (0.09 M) 95 30 g %
15 H3PO4 DMSO (0.09 M) 0
16 A H3PO4 DMSO (0.09 M) 0 h

a2.5 mol% of catalyst.

b2 equiv. of additive with respect to 1a.

cIsolated yields.

dPhenylisocyanate and benzamide are obtained.

eReaction conditions: 1a (0.34 mmol, 1 equiv.), 2a (1.7 mmol, 5 equiv.), additives (0.68 mmol, 2 equiv.) and photocatalyst (8.5 μmol, 2.5 mol%) in dry solvent (0.09 M) under N2 was irradiated with blue light for 4 h.

f1 mol% of the catalyst used.

g1 equiv. of N-methylpyrrole.

hWithout light.