Synthesis of quinolines, 2-quinolones, phenanthridines, and 6(5H)-phenanthridinones via palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitroarenes with β-halo-enals, -enones, or -esters
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Banwell, MG
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Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, AustraliaAustralian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia
Banwell, MG
[1
]
Lupton, DW
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Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, AustraliaAustralian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia
Lupton, DW
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]
Ma, XH
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Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, AustraliaAustralian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia
Ma, XH
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Renner, J
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Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, AustraliaAustralian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia
Renner, J
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]
Sydnes, MO
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Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, AustraliaAustralian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia
Sydnes, MO
[1
]
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[1] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia
Palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitrobenzene (1 R = H) and its derivatives with a range of beta-halo-enals, -enones, or -esters readily affords the corresponding beta-aryl derivatives, which are converted into the corresponding quinolines, 2-quinolones, phenanthridines, or 6(5H)-phenanthridinones on reaction with dihydrogen in the presence of Pd on C or with TiCl3 in aqueous acetone.