Journal
JOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume 694, Issue 19, Pages 3154-3159Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2009.05.016
Keywords
Aminoboron; Catalysis; Enamines; Hydroboration; Regioselectivity
Categories
Funding
- Canada Research Chairs Programme
- Canadian Foundation
- Natural Science and Engineering Research Council of Canada
- Mount Allison University
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The addition of catecholborane (HBcat, cat = 1,2-O2C6H4) to 9-vinylcarbazole can give either the branched or linear hydroboration product depending upon the judicious choice of metal catalyst used in these reactions. Analogous reactions with pinacolborane (HBpin, pin = 1,2-O2C2Me4) and HBBzpin (Bzpin = 1,2-O2C2Ph4) using catalytic amounts (5 mol%) of either Rh(acac)(dppb) or [Cp*IrCl2](2) gave the linear hydroboration product selectively. Hydroborations of 1-pyrrolidino-1-cyclopentene and 1-pyrrolidino-1-cyclohexene were complicated by a competing dehydrogenative borylation pathway. The branched isomer was not observed to any significant extent in these reactions, suggesting that the directing effect of the nitrogen atom is negligible. Although catalyzed additions of HBcat to 1-vinyl-2-pyrrolidinone gave complicated product distributions arising from competing reactions, addition of HBpin effectively generated the corresponding linear hydroboration product in good yields. (C) 2009 Elsevier B.V. All rights reserved.
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