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. 2019 Jul 18;4(7):12300–12307. doi: 10.1021/acsomega.9b01427

Table 1. Screening of Phosphorus-Based Acid Catalystsa.

graphic file with name ao-2019-01427w_0003.jpg

entry catalyst (mol %) 1a (%)b 3aa (%)b 4aa (%)b
1 (HO)P(O)H2 10 <5 >95 <5
    10c <5c 79c 13c
    5 <5 >95 <5
2 (HO)2P(O)H 10 <95 <5 <5
3 (HO)3P(O) 10 <95 <5 <5
4 (HO)P(O)(OPh)2B 10 <5 72 <5
    5 <5 72 <5
    1 14 83 <5
5 (HO)P(OPh)2 10 <5 90 5
    5 31 62 <5
    1 70 26 <5
6 (HO)P(OEt)2A 10 <5 94 <5
    5 9 84 <5
    1 47 43 <5
7 P(OPh)3 10 5 69 11
8 P(OEt)3 10 <5 67 11
a

Reaction conditions: 1a (0.5 mmol) and 2a (2 equiv) in technical cumene (0.5 mL).

b

1H NMR yields/recoveries are the average of two independent experiments and were determined with respect to 1,3,5-trimethoxybenzene as internal standard.

c

1.5 equiv of 2a.