Highly regioselective nucleophilic carbon-carbon bond formation on furans and thiophenes initiated by pummerer-type reaction

Shuji Akai; Norihito Kawashita; Hideharu Satoh; Yasufumi Wada; Keisuke Kakiguchi; Ikumi Kuriwaki; Yasuyuki Kita

doi:10.1021/ol0484310

Highly regioselective nucleophilic carbon-carbon bond formation on furans and thiophenes initiated by pummerer-type reaction

Org Lett. 2004 Oct 14;6(21):3793-6. doi: 10.1021/ol0484310.

Authors

Shuji Akai¹, Norihito Kawashita, Hideharu Satoh, Yasufumi Wada, Keisuke Kakiguchi, Ikumi Kuriwaki, Yasuyuki Kita

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan.

PMID: 15469351
DOI: 10.1021/ol0484310

Abstract

[reaction: see text] The reactions of (phenylsulfinyl)furans or -thiophenes with carbon nucleophiles in the presence of trifluoroacetic anhydride allowed the nucleophilic installation of carbon functional groups on the furan and thiophene nuclei with complete regioselectivity.