Palladium-catalyzed peri-selective chalcogenation of naphthylamines with diaryl disulfides and diselenides via C-H bond cleavage.
A palladium-catalyzed and picolinamide-directed C-H thiolation of naphthylamine derivatives with diaryl disulfides has been developed to provide a convenient route to 8-sulfenyl-1-naphthylamines. The reaction proceeds via a 5-membered palladacycle intermediates to afford the peri-thiolated products exclusively, in contrast to the conventional ortho-functionalization. Moreover, the related direct selenation was also achieved with diaryl diselenides, giving the corresponding selenated products with perfect site-selectivity.
Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University , 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan.
Masayuki
M
Iwasaki
Wataru
W
Kaneshika
Yuta
Y
Tsuchiya
Kiyohiko
K
Nakajima
Yasushi
Y
Nishihara
D015057:1-Naphthylamine / Q000737:chemistry*; D000577:Amides / Q000737:chemistry; D002384:Catalysis; D018011:Chalcogens / Q000737:chemistry*; D004220:Disulfides / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010848:Picolinic Acids / Q000737:chemistry*; D018036:Selenium Compounds / Q000737:chemistry*
D000577:Amides; D018011:Chalcogens; D004220:Disulfides; D010848:Picolinic Acids; D018036:Selenium Compounds; D010165:Palladium; D015057:1-Naphthylamine; C003142:picolinamide