TY - JOUR
T1 - TiCl4-Mediated Preparation of Thiophthalide Derivatives via Formal Thio-Passerini Reactions
AU - Ponra, Sudipta
AU - Nyadanu, Aude
AU - Kaïm, Laurent El
AU - Grimaud, Laurence
AU - Vitale, Maxime R.
N1 - Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/8/19
Y1 - 2016/8/19
N2 - By the formal extension of the Passerini reaction to thiocarbonyl derivatives, the straightforward preparation of thiophthalides is disclosed. This method involves the intermediate formation of a sulfanyl-phthalide and a titanium tetrachloride mediated isocyanide insertion reaction. When tert-butyl thiol is used, thanks to the deprotection of the tert-butyl group, a thiophthalide resulting from a 1,5-Mumm rearrangement is isolated. Owing to the multifaceted activity of TiCl4, all steps may conveniently be performed in one pot, starting directly from 2-formylbenzoic acids, tert-butyl thiol, and various isocyanides.
AB - By the formal extension of the Passerini reaction to thiocarbonyl derivatives, the straightforward preparation of thiophthalides is disclosed. This method involves the intermediate formation of a sulfanyl-phthalide and a titanium tetrachloride mediated isocyanide insertion reaction. When tert-butyl thiol is used, thanks to the deprotection of the tert-butyl group, a thiophthalide resulting from a 1,5-Mumm rearrangement is isolated. Owing to the multifaceted activity of TiCl4, all steps may conveniently be performed in one pot, starting directly from 2-formylbenzoic acids, tert-butyl thiol, and various isocyanides.
UR - https://www.scopus.com/pages/publications/84983371914
U2 - 10.1021/acs.orglett.6b01937
DO - 10.1021/acs.orglett.6b01937
M3 - Article
AN - SCOPUS:84983371914
SN - 1523-7060
VL - 18
SP - 4060
EP - 4063
JO - Organic Letters
JF - Organic Letters
IS - 16
ER -