» Articles » PMID: 35517161

Ni/Pd-catalyzed Suzuki-Miyaura Cross-coupling of Alcohols and Aldehydes and C-N Cross-coupling of Nitro and Amines Domino Redox Reactions: Base-free, Hydride Acceptor-free

Overview
Journal RSC Adv
Specialty Chemistry
Date 2022 May 6
PMID 35517161
Authors
Affiliations
Soon will be listed here.
Abstract

Domino oxidation-Suzuki-Miyaura cross-coupling of benzyl alcohols with phenylboronic acid and domino reduction-C-N cross-coupling of the nitro compounds with aryl halides were carried out using a strong Ni/Pd bimetallic redox catalyst. The catalyst bearing a copolymer with two Ni/Pd coordinated metals in porphyrin (derived from demetalated chlorophyll b) and salen-type ligands, and pyridine moiety as a base functionality all immobilized on magnetite NPs was synthesised and characterized. The domino oxidation cross-coupling reaction was accomplished under molecular O in the absence of any hydride acceptor or/and base. Also, the domino reduction C-N cross-coupling reaction was performed in the presence of NaBH without the need for any base and co-reductant. This multifunctional catalyst gave moderate to good yields for both coupling reactions with high chemoselectivity. A wide investigation was conducted to determine its mechanism and chemoselectivity.

Citing Articles

Pd/NHC catalyzed reduction and coupling of nitroaromatics for the synthesis of diarylamines.

Chen W, Chen K, Wang X, Yang L, Chen W RSC Adv. 2024; 14(24):16624-16628.

PMID: 38784423 PMC: 11110159. DOI: 10.1039/d4ra00921e.


Catalytic filtration: efficient C-C cross-coupling using Pd-salen complex-embedded cellulose filter paper as a portable catalyst.

Raya I, Danshina S, Turki Jalil A, Suksatan W, Mahmoud M, Roomi A RSC Adv. 2022; 12(31):20156-20173.

PMID: 35919614 PMC: 9274805. DOI: 10.1039/d2ra03440a.


Efficient reduction of nitro compounds and domino preparation of 1-substituted-1-1,2,3,4-tetrazoles by Pd(ii)-polysalophen coated magnetite NPs as a robust versatile nanocomposite.

Xu D, Xiong M, Kazemnejadi M RSC Adv. 2022; 11(21):12484-12499.

PMID: 35423830 PMC: 8697099. DOI: 10.1039/d1ra01164b.

References
1.
Zhuang X, Zhang H, Chikushi N, Zhao C, Oyaizu K, Chen X . Biodegradable and electroactive TEMPO-substituted acrylamide/lactide copolymers. Macromol Biosci. 2010; 10(10):1203-9. DOI: 10.1002/mabi.201000031. View

2.
Hirai Y, Tamiaki H, Kashimura S, Saga Y . Demetalation kinetics of natural chlorophylls purified from oxygenic photosynthetic organisms: effect of the formyl groups conjugated directly to the chlorin pi-macrocycle. Photochem Photobiol Sci. 2009; 8(12):1701-7. DOI: 10.1039/b9pp00018f. View

3.
Cao S, Zhang L, Chai Y, Yuan R . Electrochemistry of cholesterol biosensor based on a novel Pt-Pd bimetallic nanoparticle decorated graphene catalyst. Talanta. 2013; 109:167-72. DOI: 10.1016/j.talanta.2013.02.002. View

4.
Borah K, Bhuyan J . Magnesium porphyrins with relevance to chlorophylls. Dalton Trans. 2017; 46(20):6497-6509. DOI: 10.1039/c7dt00823f. View

5.
Chen Y, Coussanes G, Souris C, Aillard P, Kaldre D, Runggatscher K . A Domino 10-Step Total Synthesis of FR252921 and Its Analogues, Complex Macrocyclic Immunosuppressants. J Am Chem Soc. 2019; 141(35):13772-13777. PMC: 6837725. DOI: 10.1021/jacs.9b07185. View