Ortho-C-H borylation of benzoate esters with bis(pinacolato)diboron catalyzed by iridium-phosphine complexes
- PMID: 20024326
- DOI: 10.1039/b910298a
Ortho-C-H borylation of benzoate esters with bis(pinacolato)diboron catalyzed by iridium-phosphine complexes
Abstract
Iridium complexes generated from [Ir(OMe)(COD)](2) and tris[3,5-bis(trifluoromethyl)phenyl]phosphine efficiently catalyzed the ortho-C-H borylation of benzoate esters with bis(pinacolato)diboron in octane at 80 degrees C to produce the corresponding arylboronates in high yields with excellent regioselectivities.
Similar articles
-
Directed ortho borylation of functionalized arenes catalyzed by a silica-supported compact phosphine-iridium system.J Am Chem Soc. 2009 Apr 15;131(14):5058-9. doi: 10.1021/ja9008419. J Am Chem Soc. 2009. PMID: 19351202
-
Iridium-catalyzed borylation of benzene with diboron. Theoretical elucidation of catalytic cycle including unusual iridium(v) intermediate.J Am Chem Soc. 2003 Dec 24;125(51):16114-26. doi: 10.1021/ja0302937. J Am Chem Soc. 2003. PMID: 14678004
-
Vinylic C--H borylation of cyclic vinyl ethers with bis(pinacolato)diboron catalyzed by an Iridium(I)-dtbpy complex.Chem Asian J. 2008 Dec 1;3(12):2082-90. doi: 10.1002/asia.200800157. Chem Asian J. 2008. PMID: 18844313
-
Iridium(I)-catalyzed C-H Borylation of α,β-Unsaturated Esters with Bis(pinacolato)diboron.Chem Asian J. 2016 May 6;11(9):1400-5. doi: 10.1002/asia.201600078. Epub 2016 Apr 5. Chem Asian J. 2016. PMID: 26929021
-
Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes.J Am Chem Soc. 2005 Oct 19;127(41):14263-78. doi: 10.1021/ja053433g. J Am Chem Soc. 2005. PMID: 16218621
Cited by
-
A Tutorial on Selectivity Determination in C(sp2)-H Oxidative Addition of Arenes by Transition Metal Complexes.Organometallics. 2021 Apr 12;40(7):813-831. doi: 10.1021/acs.organomet.1c00030. Epub 2021 Mar 16. Organometallics. 2021. PMID: 33867622 Free PMC article. Review.
-
Outer-sphere direction in iridium C-H borylation.J Am Chem Soc. 2012 Jul 18;134(28):11350-3. doi: 10.1021/ja303443m. Epub 2012 Jul 3. J Am Chem Soc. 2012. PMID: 22703452 Free PMC article.
-
A traceless directing group for C-H borylation.Angew Chem Int Ed Engl. 2013 Dec 2;52(49):12915-9. doi: 10.1002/anie.201306511. Epub 2013 Nov 12. Angew Chem Int Ed Engl. 2013. PMID: 24222178 Free PMC article.
-
C7-derivatization of C3-alkylindoles including tryptophans and tryptamines.J Org Chem. 2014 Nov 21;79(22):11254-63. doi: 10.1021/jo502062z. Epub 2014 Nov 10. J Org Chem. 2014. PMID: 25343326 Free PMC article.
-
Scope of the two-step, one-pot palladium-catalyzed borylation/Suzuki cross-coupling reaction utilizing bis-boronic acid.J Org Chem. 2012 Oct 5;77(19):8678-88. doi: 10.1021/jo301642v. Epub 2012 Sep 20. J Org Chem. 2012. PMID: 22994557 Free PMC article.
LinkOut - more resources
Full Text Sources
Other Literature Sources
Miscellaneous