Journal
ACS CATALYSIS
Volume 7, Issue 9, Pages 5950-5954Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b01750
Keywords
hydroboration; ruthenium; borane; anti-Markovnikov addition; green synthesis
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Funding
- SERB New Delhi [EMR/2016/002517, SR/S2/RJN-64/2010]
- DAE
- NISER
- DST
- SERB
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Ruthenium-catalyzed selective hydroboration of styrenes and aliphatic olefins with pinacolborane (HBpin) is reported. This efficient transformation provided products with exclusive anti-Markovnikov selectivity, and this hydroboration protocol is compatible with olefins having electronic and steric divergence as well as diverse functional groups. Hydroboration occurred at room temperature under solvent-free conditions with minimal catalyst load (0.05 mol %) and provided high TON (>1980; >990 per Ru). Mechanistic studies confirmed the involvement of intermediate [{(eta(6)-p-cymene)RuCl}(2)(mu-H-mu-Cl)] (2). A catalytic cycle including a mononuclear ruthenium intermediate is proposed. The rationale for observed anti-Markovnikov selectivity is provided from reversible 1,3-hydride transfer leading to the regioselective 1,2-insertion on olefins.
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