期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 39, 页码 16131-16134出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja306446m
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资金
- University of Wisconsin, Madison
- NSF [CHE-9208463, CHE-9629688]
- NIH [RR08389-01]
A Cu(I)-catalyzed 1,3-halogen migration reaction effectively recycles an activating group by transferring bromine or iodine from a sp(2) to a benzylic carbon with concomitant borylation of the Ar-X bond. The resulting benzyl halide can be reacted in the same vessel under a variety of conditions to form an additional carbon-heteroatom bond. Cross-over experiments using an isotopically enriched bromide source support intramolecular transfer of Br. The reaction is postulated to proceed via a Markovnikov hydrocupration of the o-halostyrene, oxidative addition of the resulting Cu(I) complex into the Ar-X bond, reductive elimination of the new sp(3) C-X bond, and final borylation of an Ar-Cu(I) species to turn over the catalytic cycle.
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