Literature DB >> 14982422

A highly selective catalytic method for the oxidative functionalization of C-H bonds.

Allison R Dick1, Kami L Hull, Melanie S Sanford.   

Abstract

This communication describes a new and highly practical Pd(II)-catalyzed method for the regio- and chemoselective oxidative functionalization of arenes and alkanes. Carbon-hydrogen bonds of substrates that contain a variety of directing groups (e.g., pyridine, azobenzene, pyrazole, and imine derivatives) are selectively transformed into esters, ethers, and aryl-halides under mild conditions. The scope of this reaction in terms of substrate, directing group, and oxidant is described, and a preliminary catalytic cycle is proposed.

Entities:  

Year:  2004        PMID: 14982422     DOI: 10.1021/ja031543m

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  92 in total

1.  Efficient diacetoxylation of alkenes via Pd(II)/Pd(IV) process with peracetic acid and acetic anhydride.

Authors:  Chan Pil Park; Joo Ho Lee; Kyung Soo Yoo; Kyung Woon Jung
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

2.  Weak coordination as a powerful means for developing broadly useful C-H functionalization reactions.

Authors:  Keary M Engle; Tian-Sheng Mei; Masayuki Wasa; Jin-Quan Yu
Journal:  Acc Chem Res       Date:  2011-12-14       Impact factor: 22.384

3.  Overcoming the "oxidant problem": strategies to use O2 as the oxidant in organometallic C-H oxidation reactions catalyzed by Pd (and Cu).

Authors:  Alison N Campbell; Shannon S Stahl
Journal:  Acc Chem Res       Date:  2012-01-23       Impact factor: 22.384

4.  Iridium-catalyzed arene ortho-silylation by formal hydroxyl-directed C-H activation.

Authors:  Eric M Simmons; John F Hartwig
Journal:  J Am Chem Soc       Date:  2010-11-15       Impact factor: 15.419

5.  PyDipSi: a general and easily modifiable/traceless Si-tethered directing group for C-H acyloxylation of arenes.

Authors:  Natalia Chernyak; Alexander S Dudnik; Chunhui Huang; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2010-06-23       Impact factor: 15.419

6.  Studies in chlorin chemistry. 3. A practical synthesis of c,d-ring symmetric chlorins of potential utility in photodynamic therapy.

Authors:  William G O'Neal; William P Roberts; Indranath Ghosh; Hui Wang; Peter A Jacobi
Journal:  J Org Chem       Date:  2006-04-28       Impact factor: 4.354

7.  Ketone-catalyzed photochemical C(sp3)-H chlorination.

Authors:  Lei Han; Jibao Xia; Lin You; Chuo Chen
Journal:  Tetrahedron       Date:  2017-05-04       Impact factor: 2.457

8.  On the mechanism of palladium-catalyzed aromatic C-H oxidation.

Authors:  David C Powers; Daphne Y Xiao; Matthias A L Geibel; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2010-10-20       Impact factor: 15.419

9.  Pd(II)-catalyzed C-H functionalizations directed by distal weakly coordinating functional groups.

Authors:  Gang Li; Li Wan; Guofu Zhang; Dasheng Leow; Jillian Spangler; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2015-03-24       Impact factor: 15.419

10.  Pd-catalyzed C-H fluorination with nucleophilic fluoride.

Authors:  Kate B McMurtrey; Joy M Racowski; Melanie S Sanford
Journal:  Org Lett       Date:  2012-07-30       Impact factor: 6.005

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