Divergent and Chemoselective Transformations of Thioamides with Designed Carbene Equivalents

• Published in: Chemistry : a European journal Vol. 25; no. 44; pp. 10314 - 10318
• Main Authors: Saito, Masato, Kobayashi, Yusuke, Takemoto, Yoshiji
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 06.08.2019; Wiley Subscription Services, Inc
• Subjects: Aqueous solutions; Chemical compounds; Chemical reactions; Chemistry; Chemistry, Multidisciplinary; chemoselectivity; Coupling (molecular); Drugs; enaminones; halogen bonding; hypervalent compounds; Peptides; Physical Sciences; Prodrugs; Science & Technology; Steroid hormones; Steroids; Thiazoles; chemoselectivity; SUBSTITUTION; ACTIVATION; thiazoles; hypervalent compounds; PHENYLIODONIUM YLIDE; STABILITY; REACTIVITY; HALOGEN; enaminones; BETA-SHEET; IODONIUM YLIDES; ESTERS; halogen bonding; HYPERVALENT IODINE REAGENTS

The reactions of thioamides with ortho‐nitro‐substituted iodonium ylides proceeded under mild conditions to give enaminones or thiazoles, depending on the iodonium ylide used. This protocol allowed the use of protic solvents, including aqueous solutions, and therefore coupling reactions with complex...