Formation of Aryl- and Benzylboronate Esters by Rhodium-Catalyzed C-H Bond Functionalization with Pinacolborane

Shigeru Shimada; Andrei S Batsanov; Judith A K Howard; Todd B Marder

doi:10.1002/1521-3773(20010601)40:11<2168::AID-ANIE2168>3.0.CO;2-0

Formation of Aryl- and Benzylboronate Esters by Rhodium-Catalyzed C-H Bond Functionalization with Pinacolborane

Angew Chem Int Ed Engl. 2001 Jun 1;40(11):2168-2171. doi: 10.1002/1521-3773(20010601)40:11<2168::AID-ANIE2168>3.0.CO;2-0.

Authors

Shigeru Shimada¹, Andrei S Batsanov¹, Judith A K Howard¹, Todd B Marder¹

Affiliation

¹ Department of Chemistry University of Durham South Road, Durham, DH1 3LE (UK) Fax: (+44) 191-386-1127.

PMID: 29712224
DOI: 10.1002/1521-3773(20010601)40:11<2168::AID-ANIE2168>3.0.CO;2-0

Abstract

Direct borylation of C-H bonds in aromatic compounds can be achieved by using the efficient homogeneous catalyst precursor [RhCl(PiPr₃ )₂ (N₂ )] and pinacolborane (HBpin; see scheme). High selectivity for the benzyl positions, observed for toluene, p-xylene, and mesitylene, was attributed to the formation of η³ -benzyl intermediates.

Keywords: C−H activation; boron; homogeneous catalysis; phosphanes; rhodium.