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Literature DB >> 25268810

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

Raja K Rit¹, M Ramu Yadav, Koushik Ghosh, Majji Shankar, Akhila K Sahoo.

Abstract

S-methyl-S-2-pyridyl-sulfoximine (MPyS) directed bromination and chlorination of the 1°-β-C(sp(3))-H bond of MPyS-N-amides is realized under the influence of N-Br/Cl-phthalimides and a Pd(II)-catalyst. The sequential halogenation and acetoxylation of α-dimethyl MPyS-N-amides constructs highly functionalized α-trisubstituted aliphatic acid derivatives. The MPyS directing group is cleaved from the halogenated products and recovered.

Entities: Chemical Species

Year: 2014 PMID： 25268810 DOI： 10.1021/ol502337b

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

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Cited

13 in total

1. 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

2. 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

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

Authors: Ru-Yi Zhu; Luo-Yan Liu; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2017-08-29 Impact factor: 15.419

4. Diverse sp(3) C-H functionalization through alcohol β-sulfonyloxylation.

Authors: Yan Xu; Guobing Yan; Zhi Ren; Guangbin Dong
Journal: Nat Chem Date: 2015-08-24 Impact factor: 24.427

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

Review 6. 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

7. Site-selective bromination of sp³ C-H bonds.

Authors: Shyam Sathyamoorthi; Shibdas Banerjee; J Du Bois; Noah Z Burns; Richard N Zare
Journal: Chem Sci Date: 2017-11-20 Impact factor: 9.825

Review 8. sp³ C-H activation via exo-type directing groups.

Authors: Yan Xu; Guangbin Dong
Journal: Chem Sci Date: 2018-01-17 Impact factor: 9.825

9. Copper(I)-catalysed site-selective C(sp³)-H bond chlorination of ketones, (E)-enones and alkylbenzenes by dichloramine-T.

Authors: Jianwen Jin; Yichao Zhao; Sara Helen Kyne; Kaveh Farshadfar; Alireza Ariafard; Philip Wai Hong Chan
Journal: Nat Commun Date: 2021-07-01 Impact factor: 14.919

10. Transfer of Electrophilic NH Using Convenient Sources of Ammonia: Direct Synthesis of NH Sulfoximines from Sulfoxides.

Authors: Marina Zenzola; Robert Doran; Leonardo Degennaro; Renzo Luisi; James A Bull
Journal: Angew Chem Int Ed Engl Date: 2016-04-29 Impact factor: 15.336

Review 6. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Review 8. sp3 C-H activation via exo-type directing groups.

Review 6. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.

Review 8. sp³ C-H activation via exo-type directing groups.