Literature DB >> 30665300

Sequential Functionalization of meta-C-H and ipso-C-O Bonds of Phenols.

Jiancong Xu1, Jingjing Chen1, Feng Gao1, Shuguang Xie1, Xiaohua Xu1,2, Zhong Jin1,2, Jin-Quan Yu3.   

Abstract

The use of a template as a linchpin motif in directed remote C-H functionalization is a versatile yet relatively underexplored strategy. We have developed a template-directed approach to realizing one-pot sequential palladium-catalyzed meta-selective C-H olefination of phenols, and nickel-catalyzed ipso-C-O activation and arylation. Thus, this bifunctional template converts phenols to synthetically useful 1,3-disubstituted arenes.

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Year:  2019        PMID： 30665300      PMCID： PMC6586216          DOI： 10.1021/jacs.8b13403

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


  42 in total

1.  TMC-95A, B, C, and D, novel proteasome inhibitors produced by Apiospora montagnei Sacc. TC 1093. Taxonomy, production, isolation, and biological activities.

Authors:  Y Koguchi; J Kohno; M Nishio; K Takahashi; T Okuda; T Ohnuki; S Komatsubara
Journal:  J Antibiot (Tokyo)       Date:  2000-02       Impact factor: 2.649

2.  Total synthesis of TMC-95A.

Authors:  Masayuki Inoue; Hayato Sakazaki; Hidetomo Furuyama; Masahiro Hirama
Journal:  Angew Chem Int Ed Engl       Date:  2003-06-16       Impact factor: 15.336

3.  The total synthesis of proteasome inhibitors TMC-95A and TMC-95B: discovery of a new method to generate cis-propenyl amides.

Authors:  Songnian Lin; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2002-02-01       Impact factor: 15.336

4.  A concise, total synthesis of the TMC-95A/B proteasome inhibitors.

Authors:  Brian K Albrecht; Robert M Williams
Journal:  Proc Natl Acad Sci U S A       Date:  2004-05-26       Impact factor: 11.205

5.  Molecular recognition in the selective oxygenation of saturated C-H bonds by a dimanganese catalyst.

Authors:  Siddhartha Das; Christopher D Incarvito; Robert H Crabtree; Gary W Brudvig
Journal:  Science       Date:  2006-06-30       Impact factor: 47.728

Review 6.  Direct transition metal-catalyzed functionalization of heteroaromatic compounds.

Authors:  Ilya V Seregin; Vladimir Gevorgyan
Journal:  Chem Soc Rev       Date:  2007-03-05       Impact factor: 54.564

7.  Agostic interactions in transition metal compounds.

Authors:  Maurice Brookhart; Malcolm L H Green; Gerard Parkin
Journal:  Proc Natl Acad Sci U S A       Date:  2007-04-18       Impact factor: 11.205

8.  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

9.  Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate.

Authors:  Tatsuo Ishiyama; Jun Takagi; Kousaku Ishida; Norio Miyaura; Natia R Anastasi; John F Hartwig
Journal:  J Am Chem Soc       Date:  2002-01-23       Impact factor: 15.419

10.  Pd(II)-catalyzed olefination of electron-deficient arenes using 2,6-dialkylpyridine ligands.

Authors:  Yang-Hui Zhang; Bing-Feng Shi; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2009-04-15       Impact factor: 15.419
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  7 in total

1.  meta C-H Arylation of Electron-Rich Arenes: Reversing the Conventional Site Selectivity.

Authors:  Luo-Yan Liu; Jennifer X Qiao; Kap-Sun Yeung; William R Ewing; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2019-09-06       Impact factor: 15.419

Review 2.  Achieving Site-Selectivity for C-H Activation Processes Based on Distance and Geometry: A Carpenter's Approach.

Authors:  Guangrong Meng; Nelson Y S Lam; Erika L Lucas; Tyler G Saint-Denis; Pritha Verma; Nikita Chekshin; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2020-06-05       Impact factor: 15.419

3.  Rational Development of Remote C-H Functionalization of Biphenyl: Experimental and Computational Studies.

Authors:  Zhoulong Fan; Katherine L Bay; Xiangyang Chen; Zhe Zhuang; Han Seul Park; Kap-Sun Yeung; K N Houk; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-12       Impact factor: 15.336

4.  Empirical Guidelines for the Development of Remote Directing Templates through Quantitative and Experimental Analyses.

Authors:  Nelson Y S Lam; Zhoulong Fan; Kevin Wu; Han Seul Park; Su Yong Shim; Daniel A Strassfeld; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2022-02-02       Impact factor: 16.383

5.  Geminal group-directed olefinic C-H functionalization via four- to eight-membered exo-metallocycles.

Authors:  Keke Meng; Tingyan Li; Chunbing Yu; Cong Shen; Jian Zhang; Guofu Zhong
Journal:  Nat Commun       Date:  2019-11-08       Impact factor: 14.919

6.  Pd(ii)-catalyzed meta-C-H bromination and chlorination of aniline and benzoic acid derivatives.

Authors:  Hao Wang; Lei Fu; Chunlin Zhou; Gang Li
Journal:  Chem Sci       Date:  2022-07-05       Impact factor: 9.969

7.  Silanol: a bifunctional group for peptide synthesis and late-stage functionalization.

Authors:  Qi-Long Hu; Ke-Qiang Hou; Jian Li; Yang Ge; Zhen-Dong Song; Albert S C Chan; Xiao-Feng Xiong
Journal:  Chem Sci       Date:  2020-06-03       Impact factor: 9.825
  7 in total

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