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. 2021 May 10;17:1048–1085. doi: 10.3762/bjoc.17.84

Table 2.

Addition of arylboronic acids to enones accelerated by silver salts [3435].

graphic file with name Beilstein_J_Org_Chem-17-1048-i002.jpg

entry cyclic substrates Ar additive (equiv) temp. (°C) yield (%) ee (%)
n (catalyst)

1 0 (PdL1b) Ph AgBF4 0 94 94 (S)
2 1 (PdL1a) Ph AgBF4 0 90 92 (R)
3 1 (PdL1a) Ph AgBF4 (0.05) 20 99a 89 (R)
4 1 (PdL1a) 3-MeO-C6H4 AgBF4 (0.05) 20 98a 91 (R)
5 2 (PdL1a) Ph AgBF4 0 92 89 (R)

acyclic substrates
R1 R2

6 Ph Ph 4-Me-C6H4 AgBF4 (0.1) 20 73 95
7 Ph Me 3-Cl-C6H4 25 90 93
8 Ph Me 3-MeO-C6H4 AgBF4 (0.1) 0 96 95
9 Ph Me 4-MeO-C6H4 AgBF4 (0.1) 0 75 94
10 Ph Me 3,4-(CH2O2)-C6H3 0 77 95
11 Ph Me 4-MeS-C6H4 AgBF4 (0.1) 25 <10
12 Ph Me 4-Ac-C6H4 0 95 93
13 Ph n-Bu 3-MeO-C6H4 AgBF4 (0.1) 0 66 99
14 Ph iPr 3-MeO-C6H4 AgBF4 (0.1) 0 80 95
15 Ph Cy 3-MeO-C6H4 AgSbF6 (0.05) 0 93 95
16 Ph Ph 3-MeO-C6H4 AgBF4 (0.1) 0 86 97
17 Ph Ph 4-Me-C6H4 0 91 95
18 Ph 4-MeO-C6H4 3-MeO-C6H4 AgSbF6 (0.1) 0 73 95
19 Ph 3-NO2-C6H4 3-MeO-C6H4 AgSbF6 (0.2) 0 44 92
20 4-MeO-C6H4 Ph 3-MeO-C6H4 AgBF4 (0.1) 0 75 99
21 2-naphthyl Me 3-MeO-C6H4 AgBF4 (0.1) 0 99 96
22 2-BnO-5-Me-C6H3 Me Ph 0 97 96
23 Ph Ph 0 86 98
24 n-C5H11 Me Ph AgBF4 0 99 80

aReaction time: 48 h.