Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 9, Pages 3160-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja809382c
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Funding
- NSF [CHE-0715138, DBI-0619576]
- NIH [GM-47480]
- AstraZeneca Graduate Fellowship
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A Cu-catalyzed method for efficient boron-copper addition processes involving acyclic and cyclic disubstituted aryl. olefins are reported. Reactions are promoted with 0.5-5 mol % of a readily available N-heterocyclic carbene (NHC) complex; the presence of MeOH promotes in situ protonation of the C-Cu bond and leads to efficient catalyst turnover, constituting a net Cu-catalyzed hydroboration process. Reactions proceed in >98:<2 site selectivity and furnish secondary organoborane isomers that complement those obtained through reactions of boron-hydride reagents or by Rh- or Ir-catalyzed hydroborations (benzylic secondary C-B bonds). Initial observations regarding processes catalyzed by chiral NHC complexes, delivering products in up to 99:1 enantiomeric ratio, are disclosed.
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