An opportunity for Mg-catalyzed Grignard-type reactions: direct coupling of benzylic halides with pinacolborane with 10 mol % of magnesium.
Mg in catalytic amounts as the only metal permits the reductive coupling between benzyl halides and pinacolborane. HBpin acts both as an electrophile and as a reducing agent to regenerate an organomagnesium species in situ. An hydride oxidation mechanism is proposed on the basis of DFT calculations.
Pintaric
Christine
C
Laboratoire de Chimie des Molécules Bioactives et des Arômes, Université de Nice-Sophia Antipolis, CNRS-UMR 6001, Institut de Chimie de Nice, 28, avenue de Valrose F-06108 Nice, France.
Olivero
Sandra
S
Gimbert
Yves
Y
Chavant
Pierre Y
PY
Duñach
Elisabet
E
D001555:Benzene Derivatives / Q000737:chemistry*; D001880:Boranes / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003198:Computer Simulation; D008274:Magnesium / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D001555:Benzene Derivatives; D001880:Boranes; D008274:Magnesium