Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds
- PMID: 11719693
- DOI: 10.1126/science.1067074
Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds
Abstract
Arylboron compounds have intriguing properties and are important building blocks for chemical synthesis. A family of Ir catalysts now enables the direct synthesis of arylboron compounds from aromatic hydrocarbons and boranes under "solventless" conditions. The Ir catalysts are highly selective for C-H activation and do not interfere with subsequent in situ transformations, including Pd-mediated cross-couplings with aryl halides. By virtue of their favorable activities and exceptional selectivities, these Ir catalysts impart the synthetic versatility of arylboron reagents to C-H bonds in aromatic and heteroaromatic hydrocarbons.
Similar articles
-
para-C-H Borylation of Benzene Derivatives by a Bulky Iridium Catalyst.J Am Chem Soc. 2015 Apr 22;137(15):5193-8. doi: 10.1021/jacs.5b02052. Epub 2015 Apr 10. J Am Chem Soc. 2015. PMID: 25860511
-
Iridium-catalyzed C-H activation versus directed ortho metalation: complementary borylation of aromatics and heteroaromatics.Chemistry. 2010 Jul 19;16(27):8155-61. doi: 10.1002/chem.201000401. Chemistry. 2010. PMID: 20533457
-
"One-pot" tandem C-H borylation/1,4-conjugate addition/reduction sequence.Org Lett. 2010 Dec 17;12(24):5700-3. doi: 10.1021/ol102518v. Epub 2010 Nov 15. Org Lett. 2010. PMID: 21077634
-
Carbon-carbon bonding made easy.Chem Commun (Camb). 2005 Oct 14;(38):4759-63. doi: 10.1039/b507375h. Epub 2005 Sep 7. Chem Commun (Camb). 2005. PMID: 16193109 Review.
-
Rhodium-catalyzed C-H bond arylation of arenes.Top Curr Chem. 2010;292:231-80. doi: 10.1007/128_2009_12. Top Curr Chem. 2010. PMID: 21500409 Review.
Cited by
-
Base-catalyzed aryl halide isomerization enables the 4-selective substitution of 3-bromopyridines.Chem Sci. 2020 Sep 9;11(38):10517-10522. doi: 10.1039/d0sc02689a. Chem Sci. 2020. PMID: 34094310 Free PMC article.
-
Unsupported boron-carbon σ-coordination to platinum as an isolable snapshot of σ-bond activation.Nat Commun. 2012 May 29;3:872. doi: 10.1038/ncomms1884. Nat Commun. 2012. PMID: 22643899
-
Mechanism of the Arene-Limited Nondirected C-H Activation of Arenes with Palladium*.Angew Chem Int Ed Engl. 2021 Jul 5;60(28):15641-15649. doi: 10.1002/anie.202105092. Epub 2021 Jun 9. Angew Chem Int Ed Engl. 2021. PMID: 33998116 Free PMC article.
-
Arylboronic acids as versatile coupling partners in fast microwave promoted oxidative Heck chemistry.Mol Divers. 2003;7(2-4):97-106. doi: 10.1023/b:modi.0000006803.99656.8c. Mol Divers. 2003. PMID: 14870838
-
Synthesis of 1,2,3-triazoles using Grignard reactions through the protection of azides.Front Chem. 2023 Jul 31;11:1237878. doi: 10.3389/fchem.2023.1237878. eCollection 2023. Front Chem. 2023. PMID: 37583567 Free PMC article.
Publication types
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources
Other Literature Sources