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Pd‐Catalyzed Direct Arylations of Heteroarenes with Polyfluoroalkoxy‐Substituted Bromobenzenes
Author(s) -
Huang HaiYun,
Li Haoran,
Cordier Marie,
Soulé JeanFrançois,
Doucet Henri
Publication year - 2020
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.202001028
Subject(s) - chemistry , catalysis , bromide , reactivity (psychology) , aryl , palladium , ring (chemistry) , combinatorial chemistry , medicinal chemistry , base (topology) , tetra , organic chemistry , medicine , mathematical analysis , alkyl , alternative medicine , mathematics , pathology
The reactivity of di‐, tri‐ and tetra‐fluoroalkoxy‐substituted bromobenzenes in the direct arylation of 5‐membered ring heteroarenes using palladium catalysis was explored. High yields in arylated heteroarenes were obtained using only 1 mol‐% of Pd(OAc) 2 catalyst with KOAc as an inexpensive base. Similar yields were obtained with o/m/p trifluoromethoxy‐, o/p difluoromethoxy‐, and tetrafluoroethoxy‐substituents on the aryl bromide. A bromo‐substituted difluorobenzo[ d ][1,3]dioxole was successfully coupled. The major side‐products of the reaction are HBr/KOAc. Therefore, this synthetic scheme is very attractive for the access to such polyfluoroalkoxy‐containing arylated heteroaromatics in terms of cost, simplicity, and low environmental impact, compared to reactions involving arylation of heteroarenes with bromophenols followed by polyfluoroalkylation.