Double-Fold Ortho and Remote C–H Bond Activation/Borylation of BINOL: A Unified Strategy for Arylation of BINOL

A double-fold ortho and remote C–H borylation of BINOL is described. The proposed mechanisms involved electrostatically and sterically directed ortho and remote C–H activation processes, respectively. While B2eg2 (eg = ethylene glycolate) directs the C–H activation at ortho positions, a combination...

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Bibliographic Details
Published inOrganic letters Vol. 21; no. 16; pp. 6476 - 6480
Main Authors Bisht, Ranjana, Chaturvedi, Jagriti, Pandey, Gajanan, Chattopadhyay, Buddhadeb
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.08.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
META
SIMPLE SYNTHETIC APPROACH
ACTIVATION
DIRECTED ORTHO-METALATION
CHIRAL BRONSTED ACIDS
ARYL
NONCOVALENT INTERACTIONS
LIGAND
BORYLATION
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Summary:A double-fold ortho and remote C–H borylation of BINOL is described. The proposed mechanisms involved electrostatically and sterically directed ortho and remote C–H activation processes, respectively. While B2eg2 (eg = ethylene glycolate) directs the C–H activation at ortho positions, a combination of HBpin and B2pin2 activates remote C–H bonds. The strategy was combined with Suzuki arylation as a one-pot protocol for the rapid synthesis of BINOL derivatives with retention of chirality.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02347