Literature DB >> 29039962

An Epoxide-Mediated Deprotection Method for Acidic Amide Auxiliary.

Qing-Lan Pei1, Guan-Da Che1, Ru-Yi Zhu2, Jian He2, Jin-Quan Yu2.   

Abstract

A practical method for the removal of a versatile acidic amide auxiliary has been developed. Facile alcoholysis of the amide in the presence of KOAc is enabled by an epoxide, which mechanistically resembles the removal of the Myers' auxiliary. The protocol has been applied to the removal of a variety of amide substrates and their C-H functionalization products with high efficiency and low cost, representing a step forward toward the development of a versatile directing group for C-H activation.

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Year:  2017        PMID： 29039962      PMCID： PMC5710756          DOI： 10.1021/acs.orglett.7b02841

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  15 in total

1.  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

2.  Practical Pd(II)-Catalyzed C-H Alkylation with Epoxides: One-Step Syntheses of 3,4-Dihydroisocoumarins.

Authors:  Guolin Cheng; Tuan-Jie Li; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2015-08-19       Impact factor: 15.419

Review 3.  A Simple and Versatile Amide Directing Group for C-H Functionalizations.

Authors:  Ru-Yi Zhu; Marcus E Farmer; Yan-Qiao Chen; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-01       Impact factor: 15.336

4.  Ligand-accelerated enantioselective methylene C(sp3)-H bond activation.

Authors:  Gang Chen; Wei Gong; Zhe Zhuang; Michal S Andrä; Yan-Qiao Chen; Xin Hong; Yun-Fang Yang; Tao Liu; K N Houk; Jin-Quan Yu
Journal:  Science       Date:  2016-09-02       Impact factor: 47.728

5.  Ligand-Enabled Pd(II)-Catalyzed Bromination and Iodination of C(sp3)-H Bonds.

Authors:  Ru-Yi Zhu; Tyler G Saint-Denis; Ying Shao; Jian He; Joshua D Sieber; Chris H Senanayake; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2017-04-13       Impact factor: 15.419

6.  Ligand-Promoted Borylation of C(sp(3))-H Bonds with Palladium(II) Catalysts.

Authors:  Jian He; Heng Jiang; Ryosuke Takise; Ru-Yi Zhu; Gang Chen; Hui-Xiong Dai; T G Murali Dhar; Jun Shi; Hao Zhang; Peter T W Cheng; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-27       Impact factor: 15.336

7.  Ligand-enabled methylene C(sp3)-H bond activation with a Pd(II) catalyst.

Authors:  Masayuki Wasa; Kelvin S L Chan; Xing-Guo Zhang; Jian He; Masanori Miura; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2012-11-05       Impact factor: 15.419

8.  Palladium- and copper-catalyzed arylation of carbon-hydrogen bonds.

Authors:  Olafs Daugulis; Hien-Quang Do; Dmitry Shabashov
Journal:  Acc Chem Res       Date:  2009-08-18       Impact factor: 22.384

9.  Ligand-enabled γ-C-H olefination and carbonylation: construction of β-quaternary carbon centers.

Authors:  Suhua Li; Gang Chen; Chen-Guo Feng; Wei Gong; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2014-03-28       Impact factor: 15.419

10.  Ligand-promoted alkylation of C(sp3)-H and C(sp2)-H bonds.

Authors:  Ru-Yi Zhu; Jian He; Xiao-Chen Wang; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2014-09-15       Impact factor: 15.419
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  1 in total

1.  Enantioselective C-H Arylation and Vinylation of Cyclobutyl Carboxylic Amides.

Authors:  Qing-Feng Wu; Xiao-Bing Wang; Peng-Xiang Shen; Jin-Quan Yu
Journal:  ACS Catal       Date:  2018-02-05       Impact factor: 13.084
  1 in total

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