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. 2023 Mar 3;88(10):6476–6488. doi: 10.1021/acs.joc.3c00083

Table 1. Selected Optimization Studies for the Reaction of Oxetane Acid 1 with Ethyl Acrylate.

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    yield (%)a
entry change from standard conditions 2a 2a′ 3 4
1b none 61 (58) 8 (8) 1 1
2 cat. = Ru(bpy)3(PF6)2 <5 0 2 0
3 cat. = Mes-Acr+ 0 0 0 0
4 0.5 mol % Ir cat. 46 11 2 0
5 28 °C (fan cooling) 54 11 3 0
6 solvent = MeCN 41 7 2 1
7 solvent = 1,4-dioxane 28 3 3 1
8 [0.1 M] 59 15 2 3
9 2.0 equiv of acrylate 59 7 1 1
10 0.7 equiv of acrylate 59c 8c 2 3
11 DBU as base 39 4c 2 1
12 no photocatalyst 0 0 0 0
13 no light 0 0 0 0
14 no base 0 0 0 0
a

Reactions run on a 0.2 mmol scale under argon. Yield calculated by analysis of the 1H NMR spectrum of the crude mixture of the reaction using 1,3,5-trimethoxybenzene as internal standard and a 30 s relaxation delay (d1).

b

Reported yields are the mean average of 6 experiments, isolated yields of a single run are in parentheses.

c

Yields vs ethyl acrylate.