CuX2-mediated halolactonization reaction of monoesters of 1,2-allenyl phosphonic acids and their Suzuki cross-coupling reaction.
CuX(2)-mediated (X = Cl, Br) halolactonization of monoesters of 1,2-allenyl phosphonic acids is presented. The reaction proceeded smoothly under the mild condition for differently substituted allenic substrates giving the 4-halo-2,5-dihydro[1,2]oxaphosphole 2-oxides in good yields. The Suzuki cross-coupling reaction of these bromides and even chlorides with organic boronic acids under the catalysis of PdCl(2)(Sphos)(2) afforded 4-substituted-2,5-dihydro[1,2]oxaphosphole 2-oxides in moderate to good yields.
Yu
Fei
F
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, People's Republic of China.
Lian
Xiongdong
X
Zhao
Jinbo
J
Yu
Yihua
Y
Ma
Shengming
S
D000466:Alkadienes / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis; D007783:Lactones / Q000138:chemical synthesis*; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry*
D000466:Alkadienes; D001965:Bromides; D006846:Hydrocarbons, Halogenated; D007783:Lactones; D063065:Organophosphonates; C408079:cupric bromide; C025947:propadiene; D003300:Copper; C029892:cupric chloride