Literature DB >> 34498633

Ligand switchable site selectivity in C-H alkenylation of thiophenes by turnover-limiting step control.

Rebecca Evans1, Jessica Sampson1,2, Long Wang1, Lukas Lückemeier1, Brad P Carrow2.   

Abstract

The origin of switchable site selectivity during Pd-catalysed C-H alkenylation of heteroarenes has been examined through More O'Ferrall-Jencks, isotope effect, and DFT computational analyses, which indicate substitution of ionic thioether for pyridine dative ligands induces a change from selectivity-determining C-H cleavage to C-C bond formation, respectively.

Entities:  

Year:  2021        PMID： 34498633      PMCID： PMC9277825          DOI： 10.1039/d1cc03456a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.065


  23 in total

1.  C-H activation for the construction of C-B bonds.

Authors:  Ibraheem A I Mkhalid; Jonathan H Barnard; Todd B Marder; Jaclyn M Murphy; John F Hartwig
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

2.  Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds.

Authors:  Jian-Yang Cho; Man Kin Tse; Daniel Holmes; Robert E Maleczka; Milton R Smith
Journal:  Science       Date:  2001-11-22       Impact factor: 47.728

3.  Towards ideal synthesis: alkenylation of aryl C-H bonds by a Fujiwara-Moritani reaction.

Authors:  Lihong Zhou; Wenjun Lu
Journal:  Chemistry       Date:  2013-12-16       Impact factor: 5.236

4.  Predictable and site-selective functionalization of poly(hetero)arene compounds by palladium catalysis.

Authors:  David Lapointe; Thomas Markiewicz; Christopher J Whipp; Amy Toderian; Keith Fagnou
Journal:  J Org Chem       Date:  2010-12-01       Impact factor: 4.354

5.  Rhodium-catalyzed intermolecular C-H silylation of arenes with high steric regiocontrol.

Authors:  Chen Cheng; John F Hartwig
Journal:  Science       Date:  2014-02-21       Impact factor: 47.728

Review 6.  C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals.

Authors:  Junichiro Yamaguchi; Atsushi D Yamaguchi; Kenichiro Itami
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-06       Impact factor: 15.336

7.  Iridium-Catalyzed Silylation of Five-Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl-Imidazoline Ligand.

Authors:  Caleb Karmel; Camille Z Rubel; Elena V Kharitonova; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-18       Impact factor: 15.336

8.  Sterically Controlled C-H Olefination of Heteroarenes.

Authors:  Hao Chen; Mirxan Farizyan; Francesca Ghiringhelli; Manuel van Gemmeren
Journal:  Angew Chem Int Ed Engl       Date:  2020-05-14       Impact factor: 15.336

9.  Catalyst-Controlled Regiodivergent C-H Alkynylation of Thiophenes*.

Authors:  Arup Mondal; Manuel van Gemmeren
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-09       Impact factor: 16.823
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  1 in total

1.  Site-Selective Pd-Catalyzed C(sp3 )-H Arylation of Heteroaromatic Ketones.

Authors:  Anton Kudashev; Olivier Baudoin
Journal:  Chemistry       Date:  2021-11-11       Impact factor: 5.020
  1 in total

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