Selective synthesis of 2,3-disubstituted-2H-isoindol-1-ylphosphonate and 2,3-disubstituted-1,2-dihydroiso-quinolin-1-ylphosphonate via metal-tuned reaction of alpha-amino (2-alkynylphenyl)methylphosphonate.
Palladium(II)-catalyzed reaction of alpha-amino (2-alkynylphenyl)methylphosphonate provides a novel and efficient route to 2,3-disubstituted-2H-isoindol-1-ylphosphonate via 5-exo-cyclization and [1,5]-H shift; while 2,3-disubstituted-1,2-dihydroisoquinolin-1-ylphosphonate is afforded through 6-endo-cyclization utilizing silver triflate as catalyst.
Ding
Qiuping
Q
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, People's Republic of China.
Ye
Yang
Y
Fan
Renhua
R
Wu
Jie
J
D000097:Acetonitriles / Q000737:chemistry; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D008670:Metals / Q000737:chemistry*; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry
C521844:1,2-dihydroiso-quinolin-1-yl phosphonate; D000097:Acetonitriles; D007211:Indoles; D007546:Isoquinolines; D008670:Metals; D063065:Organophosphonates; D009943:Organophosphorus Compounds