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. 2020 Aug 13;25(16):3684. doi: 10.3390/molecules25163684

Table 1.

Oxidative cross-coupling using transition metal catalysts to form phosphoramidates.

graphic file with name molecules-25-03684-i001.jpg
Route Catalyst Reaction Conditions R R’, R’’ Yield Range/% Ref.
a 20 mol% CuI MeCN, 55 °C Me, Et, i-Pr H, alkyl 16–98 [103]
b 5 mol% CuBr EtOAc, 20 °C Et, i-Pr, Bu H, Ph, functional Ph 20–94 [104]
c 15 mol% Fe3O4@MgO CCl4, 20 °C Et, i-Pr H, Ph, Bn, cycloalkyl 52–85 [105]
d 200 mol% CuCl2 Acetone, Cs2CO3, 20 °C Me, Et, Pr, i-Pr H, alkyl 25–93 [106]
e 10 mol% Cu(OAc)2 Toluene, K2CO3, mol. sieve, 80 °C Me, Et, i-Pr, Bu RCOR a 52–99 [107]
f 2 mol% CuBr EtOAc, 25 °C Me, Et, i-Pr, Bu, Ph H, alkyl, cycloalkyl, R b 86–96 [108]
g 5 mol% Cu(OAc)2 MeOH, NaN3, 20 °C Et c R-B(OH)2 d 67–93 [109]

a urea, oxazolidinone, indole, pyrrolidinone, lactam, and sulfonamide derivatives; b methyl alaninate; c triethyl phosphite; d phenylboronic acid and phenylboronic ester derivatives.