Morita-Baylis-Hillman reaction employing N-alkylquinolinium salts as electrophiles has been developed. The reaction is promoted by DBU, which acts both as a catalyst activating the electron-poor olefin as well as a base. The dearomatization occurs regioselectively at the C-2 position, delivering a broad range of alpha-(1,2-dihydroquinolin-2-yl)vinyl esters, ketones, and sulfones. The scope of the transformation has also been extended to N-alkylpyridinium salts. For this class of substrates a presence of at least moderately electron-withdrawing substituent in the ring is necessary to attain good reactivity. In particular, N-alkylpyridinium salts containing an ester group undergo the dearomatization regioselectively at the C-4 position, while nitrile and nitro moieties cause the non-selective formation of products of the C-2 and C-6 additions.
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Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R ChinaChinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
Sun, Zhankui
Yu, Shouyun
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Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R ChinaChinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
Yu, Shouyun
Ding, Zuoding
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Ding, Zuoding
Ma, Dawei
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Wang, Yan
Liu, Yunlong
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Liu, Yunlong
Zhang, Dongdong
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Zhang, Dongdong
Wei, Hao
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Wei, Hao
Shi, Min
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Wang, Feijun
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Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R ChinaChinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
Wei, Yin
Shi, Min
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Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R ChinaChinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
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Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R ChinaChinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
Sun, Zhankui
Yu, Shouyun
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Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R ChinaChinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
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Ding, Zuoding
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Ma, Dawei
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Wang, Yan
Liu, Yunlong
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Liu, Yunlong
Zhang, Dongdong
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Zhang, Dongdong
Wei, Hao
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Shanghai Jiao Tong Univ, Sch Elect Informat & Elect Engn, Shanghai 200240, Peoples R ChinaE China Univ Sci & Technol, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China
Wei, Hao
Shi, Min
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E China Univ Sci & Technol, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China
E China Univ Sci & Technol, Inst Fine Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China
Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 354 Fenglin Rd, Shanghai 200032, Peoples R ChinaE China Univ Sci & Technol, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China
Shi, Min
Wang, Feijun
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Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R ChinaChinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
Wei, Yin
Shi, Min
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