Literature DB >> 28844134

Highly Versatile β-C(sp3)-H Iodination of Ketones Using a Practical Auxiliary.

Ru-Yi Zhu1, Luo-Yan Liu1, Jin-Quan Yu1.   

Abstract

The first example of palladium(II)-catalyzed β-C(sp3)-H iodination of a wide range of ketones using a commercially available aminooxyacetic acid auxiliary has been achieved. This L, X-type directing group overcomes the limitations of the transient directing group approach for C(sp3)-H functionalization of ketones. Practical advantages of this method include simple installation of the auxiliary without chromatography, exceptional tolerance of α-functional groups, as well as alkenes and alkynes, and rapid access to diverse sterically hindered quaternary centers.

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Year:  2017        PMID： 28844134      PMCID： PMC5710739          DOI： 10.1021/jacs.7b06851

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


  25 in total

1.  Explorations into new reaction chemistry.

Authors:  Teruaki Mukaiyama
Journal:  Angew Chem Int Ed Engl       Date:  2004-10-25       Impact factor: 15.336

2.  Palladium-catalyzed asymmetric iodination of unactivated C-H bonds under mild conditions.

Authors:  Ramesh Giri; Xiao Chen; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2005-03-29       Impact factor: 15.336

3.  Sulfoximine assisted Pd(II)-catalyzed bromination and chlorination of primary β-C(sp3)-H bond.

Authors:  Raja K Rit; M Ramu Yadav; Koushik Ghosh; Majji Shankar; Akhila K Sahoo
Journal:  Org Lett       Date:  2014-09-30       Impact factor: 6.005

4.  Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

Authors:  Jian He; Masayuki Wasa; Kelvin S L Chan; Qian Shao; Jin-Quan Yu
Journal:  Chem Rev       Date:  2016-12-02       Impact factor: 60.622

5.  Intermolecular amidation of unactivated sp2 and sp2 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion.

Authors:  Hung-Yat Thu; Wing-Yiu Yu; Chi-Ming Che
Journal:  J Am Chem Soc       Date:  2006-07-19       Impact factor: 15.419

6.  Converting gem-dimethyl groups into cyclopropanes via Pd-catalyzed sequential C-H activation and radical cyclization.

Authors:  Ramesh Giri; Masayuki Wasa; Steven P Breazzano; Jin-Quan Yu
Journal:  Org Lett       Date:  2006-12-07       Impact factor: 6.005

7.  Catalytic C-H Arylation of Aliphatic Aldehydes Enabled by a Transient Ligand.

Authors:  Ke Yang; Qun Li; Yongbing Liu; Guigen Li; Haibo Ge
Journal:  J Am Chem Soc       Date:  2016-09-26       Impact factor: 15.419

8.  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

9.  Organic chemistry. Functionalization of C(sp3)-H bonds using a transient directing group.

Authors:  Fang-Lin Zhang; Kai Hong; Tuan-Jie Li; Hojoon Park; Jin-Quan Yu
Journal:  Science       Date:  2016-01-15       Impact factor: 47.728

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
View more
  7 in total

1.  Versatile Alkylation of (Hetero)Aryl Iodides with Ketones via β-C(sp3)-H Activation.

Authors:  Ru-Yi Zhu; Luo-Yan Liu; Han Seul Park; Kai Hong; Yongwei Wu; Chris H Senanayake; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2017-11-03       Impact factor: 15.419

2.  Distal γ-C(sp3 )-H Olefination of Ketone Derivatives and Free Carboxylic Acids.

Authors:  Han Seul Park; Zhoulong Fan; Ru-Yi Zhu; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-05       Impact factor: 15.336

Review 3.  Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Authors:  Bin Liu; Andrew M Romine; Camille Z Rubel; Keary M Engle; Bing-Feng Shi
Journal:  Chem Rev       Date:  2021-10-29       Impact factor: 60.622

4.  Ligand-Enabled γ-C(sp3)-H Activation of Ketones.

Authors:  Ru-Yi Zhu; Zi-Qi Li; Han Seul Park; Chris H Senanayake; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2018-03-02       Impact factor: 15.419

5.  Photoexcited Pd(ii) auxiliaries enable light-induced control in C(sp3)-H bond functionalisation.

Authors:  Milena L Czyz; Geethika K Weragoda; Tyra H Horngren; Timothy U Connell; Daniel Gomez; Richard A J O'Hair; Anastasios Polyzos
Journal:  Chem Sci       Date:  2020-01-23       Impact factor: 9.825

6.  A direct route to six and seven membered lactones via γ-C(sp3)-H activation: a simple protocol to build molecular complexity.

Authors:  Jayabrata Das; Pravas Dolui; Wajid Ali; Jyoti Prasad Biswas; Hediyala B Chandrashekar; Gaurav Prakash; Debabrata Maiti
Journal:  Chem Sci       Date:  2020-08-19       Impact factor: 9.825

7.  β C-H di-halogenation via iterative hydrogen atom transfer.

Authors:  Ethan A Wappes; Avassaya Vanitcha; David A Nagib
Journal:  Chem Sci       Date:  2018-04-30       Impact factor: 9.825
  7 in total

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