Transition-Metal-Free Site-Selective γ-C(sp 2 )-H Monoiodination of Arenes Directed by an Aliphatic Keto Group.

Autor: Bian HL; State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.; School of Pharmacy, Lanzhou University, Lanzhou 730000, China., Tang SZ; State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China., Chen ME; State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China., Zhang XM; State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China., Lv JW; State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China., Chen XW; State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China., Qi FM; State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China., Chen SW; School of Pharmacy, Lanzhou University, Lanzhou 730000, China., Zhang FM; State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2020 Jul 17; Vol. 22 (14), pp. 5314-5319. Date of Electronic Publication: 2020 Jun 26.
DOI: 10.1021/acs.orglett.0c01466
Abstrakt: A general γ-C(sp 2 )-H iodination method directed by an aliphatic keto group has been developed under transition-metal-free conditions for the first time, generating iodoarenes in good to excellent yields with excellent site selectivity. This protocol features a wide range of aryl-substituted ketones, short reaction times, mild reaction conditions, and scalable synthetic procedures. A possible reaction mechanism was also proposed based on several control experiments.
Databáze: MEDLINE