Journal
ACS CATALYSIS
Volume 6, Issue 11, Pages 7585-7589Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b02654
Keywords
iron; borylation; dehydrogenative; vinylarenes; homogeneous catalysis
Categories
Funding
- National University of Singapore [R-143-000-614-133]
- NUS Young Investigator Award [R-143-000-630-133]
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We report the dehydrogenative borylation of vinylarenes with pinacolborane (HBpin) catalyzed by an iron(0) complex (PMe3)(4)Fe. A variety of monosubstituted and disubstituted vinylarenes underwent this iron-catalyzed transformation, affording E-vinyl boronate esters (VBEs) selectively in high yields. In addition, we coupled this iron-catalyzed dehydrogenative borylation with further transformations of the resulting vinyl boronate esters and developed various one-pot procedures for the functionalization of the vinylic C-H bonds in vinylarenes. Mechanistic studies reveal that this Fe-catalyzed reaction proceeds through syn-insertion of vinylarenes into a Fe-boryl species followed by beta-hydrogen elimination from a syn coplanar conformation of the borylalkyl iron intermediate.
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