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Literature DB >> 23955553

Controllable Mono-/Dialkenylation of Benzyl Thioethers through Rh-Catalyzed Aryl C-H Activation.

Xi-Sha Zhang¹, Qi-Lei Zhu, Yun-Fei Zhang, Yan-Bang Li, Zhang-Jie Shi.

Abstract

Under solvent control: Benzyl thioethers were alkenylated in excellent yields with broad substrate scope and the selectivity (mono- vs. disubstituted product) was controlled by the solvent and ratio of reactants. Sequential alkenylation with two different alkenes was also carried out in a one-pot process. In addition, the thioether directing group was removed in a one-pot process with simultaneous hydrogenation of the double bond to give the toluene derivatives.

Entities: Chemical

Keywords: CH activation; alkenylation; rhodium; thioethers

Year: 2013 PMID： 23955553 DOI： 10.1002/chem.201300829

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

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Cited

10 in total

1. Base-Assisted C-H Bond Cleavage in Cross-Coupling: Recent Insights into Mechanism, Speciation, and Cooperativity.

Authors: Brad P Carrow; Jessica Sampson; Long Wang
Journal: Isr J Chem Date: 2019-12-13 Impact factor: 3.333

2. Mechanistic study of enantioselective Pd-catalyzed C(sp³)-H activation of thioethers involving two distinct stereomodels.

Authors: Tyler G Saint-Denis; Nelson Y S Lam; Nikita Chekshin; Paul F Richardson; Jason S Chen; Jeff Elleraas; Kevin D Hesp; Daniel C Schmitt; Yajing Lian; Chan Woo Huh; Jin-Quan Yu
Journal: ACS Catal Date: 2021-07-19 Impact factor: 13.700

3. Ir(iii)-catalyzed thioether directed arene C-H alkenylation.

Authors: Chen Li; Xian Chen; Rui-Peng Bao; Dong-Li Li; Kun Zhang; Dong-Hui Wang
Journal: RSC Adv Date: 2019-09-24 Impact factor: 4.036

Review 4. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors: Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal: Chem Soc Rev Date: 2018-08-28 Impact factor: 54.564

5. Monoselective o-C-H Functionalizations of Mandelic Acid and α-Phenylglycine.

Authors: Navid Dastbaravardeh; Tetsuya Toba; Marcus E Farmer; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2015-07-30 Impact factor: 15.419

6. Palladium(ii)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of carbon-sulfur and carbon-hydrogen bonds.

Authors: Mamoru Tobisu; Yoshihiro Masuya; Katsuaki Baba; Naoto Chatani
Journal: Chem Sci Date: 2016-01-21 Impact factor: 9.825

Controllable Mono-/Dialkenylation of Benzyl Thioethers through Rh-Catalyzed Aryl C-H Activation.

1. Base-Assisted C-H Bond Cleavage in Cross-Coupling: Recent Insights into Mechanism, Speciation, and Cooperativity.

2. Mechanistic study of enantioselective Pd-catalyzed C(sp³)-H activation of thioethers involving two distinct stereomodels.

3. Ir(iii)-catalyzed thioether directed arene C-H alkenylation.

Review 4. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

5. Monoselective o-C-H Functionalizations of Mandelic Acid and α-Phenylglycine.

6. Palladium(ii)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of carbon-sulfur and carbon-hydrogen bonds.

7. Rh(iii)-catalyzed C-H olefination of N-pentafluoroaryl benzamides using air as the sole oxidant.

8. Rhodium catalyzed template-assisted distal para-C-H olefination.

9. Thioether-enabled palladium-catalyzed atroposelective C-H olefination for N-C and C-C axial chirality.

Review 10. Transition-metal-catalyzed remote C-H functionalization of thioethers.