PMID- 24595886 OWN - NLM STAT- MEDLINE DCOM- 20141124 LR - 20140313 IS - 1477-0539 (Electronic) IS - 1477-0520 (Linking) VI - 12 IP - 14 DP - 2014 Apr 14 TI - Direct sp3 C-H bond arylation, alkylation, and amidation of tetrahydroisoquinolines mediated by hypervalent iodine(III) under mild conditions. PG - 2189-92 LID - 10.1039/c3ob42354a [doi] AB - We have developed a method for the sp(3) C-H bond functionalization of tetrahydroisoquinolines (THIQs) mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA). The treatment of the THIQs with various nucleophiles in the presence of PIFA in a green solvent alternative gave the coupled products, with a C-C, C-N, or quaternary carbon center in high yields. FAU - Muramatsu, Wataru AU - Muramatsu W AD - Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki, Nagasaki 852-8521, Japan. muramatu@nagasaki-u.ac.jp. FAU - Nakano, Kimihiro AU - Nakano K FAU - Li, Chao-Jun AU - Li CJ LA - eng PT - Journal Article PT - Research Support, Non-U.S. Gov't PL - England TA - Org Biomol Chem JT - Organic & biomolecular chemistry JID - 101154995 RN - 0 (Amides) RN - 0 (Tetrahydroisoquinolines) RN - 9679TC07X4 (Iodine) SB - IM MH - Alkylation MH - Amides/*chemical synthesis/chemistry MH - Iodine/*chemistry MH - Molecular Structure MH - Tetrahydroisoquinolines/*chemistry EDAT- 2014/03/07 06:00 MHDA- 2014/12/15 06:00 CRDT- 2014/03/06 06:00 PHST- 2014/03/06 06:00 [entrez] PHST- 2014/03/07 06:00 [pubmed] PHST- 2014/12/15 06:00 [medline] AID - 10.1039/c3ob42354a [doi] PST - ppublish SO - Org Biomol Chem. 2014 Apr 14;12(14):2189-92. doi: 10.1039/c3ob42354a.