Premium
In situ Generation of Hypervalent Iodine Reagents for the Electrophilic Chlorination of Arenes
Author(s) -
Granados Albert,
Jia Zhiyu,
Olmo Marc,
Vallribera Adelina
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900237
Subject(s) - chemistry , hypervalent molecule , electrophile , reagent , in situ , iodine , chlorine , iodine monochloride , combinatorial chemistry , organic chemistry , catalysis
Efficient metal‐free methods for the electrophilic chlorination of arenes using PIFA and simple chlorine sources are reported. The in situ formation of PhI(Cl)OCOCF 3 from PIFA and KCl is proposed, which resulted in a chlorinating species for moderately activated arenes. Moreover, the in situ formation of PhICl 2 from PIFA and TMSCl resulted in an excellent approach for the chlorination of a great variety of arenes (20 examples) in high yields, even when working on a multigram scale.