期刊
ORGANOMETALLICS
卷 34, 期 19, 页码 4775-4780出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.organomet.5b00631
关键词
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资金
- National Institutes of Health [GM46059]
- National Science Foundation [2010094243, CHE 0946721]
A thorough investigation of the challenging Pd-catalyzed fluorination of five-membered heteroaryl bromides is presented. Crystallographic studies and density functional theory (DFT) calculations suggest that the challenging step of this transformation is C-F reductive elimination of five-membered heteroaryl fluorides from Pd(II) complexes. On the basis of these studies, we have found that various heteroaryl bromides bearing phenyl groups in the ortho position can be effectively fluorinated under catalytic conditions. Highly activated 2-bromoazoles, such as 8-bromocaffeine, are also viable substrates for this reaction.
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