Manganese-catalyzed C-C and C-N Bond Formation with Alcohols Via Borrowing Hydrogen or Hydrogen Auto-transfer

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2024 Jun 18

PMID 38887586

Authors

Mohd Farhan Ansari

Atul Kumar Maurya

Abhishek Kumar

Saravanakumar Elangovan

Affiliations

Soon will be listed here.

Abstract

Transition-metal-mediated "borrowing hydrogen" also known as hydrogen auto-transfer reactions allow the sustainable construction of C-C and C-N bonds using alcohols as hydrogen donors. In recent years, manganese complexes have been explored as efficient catalysts in these reactions. This review highlights the significant progress made in manganese-catalyzed C-C and C-N bond-formation reactions via hydrogen auto-transfer, emphasizing the importance of this methodology and manganese catalysts in sustainable synthesis strategies.

References

Reed-Berendt B, Polidano K, Morrill L . Recent advances in homogeneous borrowing hydrogen catalysis using earth-abundant first row transition metals. Org Biomol Chem. 2018; 17(7):1595-1607. DOI: 10.1039/c8ob01895b. View

Horton D, Bourne G, Smythe M . The combinatorial synthesis of bicyclic privileged structures or privileged substructures. Chem Rev. 2003; 103(3):893-930. DOI: 10.1021/cr020033s. View

Bruneau-Voisine A, Pallova L, Bastin S, Cesar V, Sortais J . Manganese catalyzed α-methylation of ketones with methanol as a C1 source. Chem Commun (Camb). 2018; 55(3):314-317. DOI: 10.1039/c8cc08064j. View

Das K, Barman M, Maji B . Advancements in multifunctional manganese complexes for catalytic hydrogen transfer reactions. Chem Commun (Camb). 2021; 57(69):8534-8549. DOI: 10.1039/d1cc02512k. View

Jafarzadeh M, Sobhani S, Gajewski K, Kianmehr E . Recent advances in /-alkylation with alcohols through hydride transfer strategies. Org Biomol Chem. 2022; 20(39):7713-7745. DOI: 10.1039/d2ob00706a. View

Babu R, Sukanya Padhy S, Kumar R, Balaraman E . Catalytic Amination of Alcohols Using Diazo Compounds under Manganese Catalysis Through Hydrogenative N-Alkylation Reaction. Chemistry. 2023; 29(61):e202302007. DOI: 10.1002/chem.202302007. View

Kalck P, Urrutigoity M . Tandem Hydroaminomethylation Reaction to Synthesize Amines from Alkenes. Chem Rev. 2018; 118(7):3833-3861. DOI: 10.1021/acs.chemrev.7b00667. View

Hofmann N, Homberg L, Hultzsch K . Synthesis of Tetrahydroquinolines via Borrowing Hydrogen Methodology Using a Manganese PN Pincer Catalyst. Org Lett. 2020; 22(20):7964-7970. PMC: 7587143. DOI: 10.1021/acs.orglett.0c02905. View

Nixon T, Whittlesey M, Williams J . Transition metal catalysed reactions of alcohols using borrowing hydrogen methodology. Dalton Trans. 2009; (5):753-62. DOI: 10.1039/b813383b. View

10.

Huang F, Liu Z, Yu Z . C-Alkylation of Ketones and Related Compounds by Alcohols: Transition-Metal-Catalyzed Dehydrogenation. Angew Chem Int Ed Engl. 2015; 55(3):862-75. DOI: 10.1002/anie.201507521. View

11.

Guillena G, Ramon D, Yus M . Hydrogen autotransfer in the N-alkylation of amines and related compounds using alcohols and amines as electrophiles. Chem Rev. 2009; 110(3):1611-41. DOI: 10.1021/cr9002159. View

12.

Somei M, Yamada F . Simple indole alkaloids and those with a nonrearranged monoterpenoid unit. Nat Prod Rep. 2004; 21(2):278-311. DOI: 10.1039/b212257j. View

13.

Shiri M . Indoles in multicomponent processes (MCPs). Chem Rev. 2012; 112(6):3508-49. DOI: 10.1021/cr2003954. View

14.

Huang M, Li Y, Li Y, Liu J, Shu S, Liu Y . Room temperature N-heterocyclic carbene manganese catalyzed selective N-alkylation of anilines with alcohols. Chem Commun (Camb). 2019; 55(44):6213-6216. DOI: 10.1039/c9cc02989c. View

15.

Saini P, Dolui P, Nair A, Verma A, Elias A . A Bench-stable 8-Aminoquinoline Derived Phosphine-free Manganese (I)-Catalyst for Environmentally Benign C(α)-Alkylation of Oxindoles with Secondary and Primary Alcohols. Chem Asian J. 2023; 18(6):e202201148. DOI: 10.1002/asia.202201148. View

16.

Ruiz-Castillo P, Buchwald S . Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions. Chem Rev. 2016; 116(19):12564-12649. PMC: 5070552. DOI: 10.1021/acs.chemrev.6b00512. View

17.

Kabadwal L, Das J, Banerjee D . Mn(ii)-catalysed alkylation of methylene ketones with alcohols: direct access to functionalised branched products. Chem Commun (Camb). 2018; 54(100):14069-14072. DOI: 10.1039/c8cc08010k. View

18.

Jana A, Kumar A, Maji B . Manganese catalyzed C-alkylation of methyl N-heteroarenes with primary alcohols. Chem Commun (Camb). 2021; 57(24):3026-3029. DOI: 10.1039/d1cc00181g. View

19.

Schlagbauer M, Kallmeier F, Irrgang T, Kempe R . Manganese-Catalyzed β-Methylation of Alcohols by Methanol. Angew Chem Int Ed Engl. 2019; 59(4):1485-1490. PMC: 7003965. DOI: 10.1002/anie.201912055. View

20.

Rana J, Gupta V, Balaraman E . Manganese-catalyzed direct C-C coupling of α-C-H bonds of amides and esters with alcohols via hydrogen autotransfer. Dalton Trans. 2019; 48(21):7094-7099. DOI: 10.1039/c8dt05020a. View