Divergent Synthesis of Benzo4,5imidazo2,1-b1,3thiazines and α-Trifluoromethyl-β-arylthio Tertiary Alcohols from 2-Mercaptobenzimidazoles and α-CF3 Alkenes

An efficient and metal-free approach for the divergent synthesis of 2-fluoro-3-aryl-4H-benzo[4,5]imidazo[2,1-b][1,3]thiazines and α-trifluoromethyl-β-arylthio tertiary alcohols from 2-mercaptoimidazoles and α-CF3 alkenes has been developed. The chemoselectivity was well controlled by base or light;...

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Veröffentlicht in:Organic letters 2024-11, Vol.26 (44), p.9610
Hauptverfasser: Wang, Bin, Lin, Honghe, Chen, Ziren, Zhang, Yonghong, Xue, Fei, Xia, Yu, Wu, Shaofeng, Jin, Weiwei, Liu, Chenjiang
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Sprache:eng
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Zusammenfassung:An efficient and metal-free approach for the divergent synthesis of 2-fluoro-3-aryl-4H-benzo[4,5]imidazo[2,1-b][1,3]thiazines and α-trifluoromethyl-β-arylthio tertiary alcohols from 2-mercaptoimidazoles and α-CF3 alkenes has been developed. The chemoselectivity was well controlled by base or light; a series of 2-fluoro-3-aryl-4H-benzo[4,5]imidazo[2,1-b][1,3]thiazines were afforded via base-mediated sequential SN2'- and SNV-type reactions. Meanwhile, α-trifluoromethyl-β-arylthio tertiary alcohols could be selectively achieved through visible-light-driven and electron donor-acceptor (EDA) complex-initiated radical cascade thiolation/hydroxylation in the absence of base, transition metal, and external photocatalyst.An efficient and metal-free approach for the divergent synthesis of 2-fluoro-3-aryl-4H-benzo[4,5]imidazo[2,1-b][1,3]thiazines and α-trifluoromethyl-β-arylthio tertiary alcohols from 2-mercaptoimidazoles and α-CF3 alkenes has been developed. The chemoselectivity was well controlled by base or light; a series of 2-fluoro-3-aryl-4H-benzo[4,5]imidazo[2,1-b][1,3]thiazines were afforded via base-mediated sequential SN2'- and SNV-type reactions. Meanwhile, α-trifluoromethyl-β-arylthio tertiary alcohols could be selectively achieved through visible-light-driven and electron donor-acceptor (EDA) complex-initiated radical cascade thiolation/hydroxylation in the absence of base, transition metal, and external photocatalyst.
ISSN:1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c03765