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Ligand-Controlled Ruthenium-Catalyzed Borrowing-Hydrogen and Interrupted-Borrowing-Hydrogen Methodologies: Functionalization of Ketones Using Methanol as a C1 Source
被引:9
作者:

Biswal, Priyabrata
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OCC Homi Bhabha Natl Inst, Natl Inst Sci Educ & Res, Sch Chem Sci, Bhubaneswar 752050, Odisha, India OCC Homi Bhabha Natl Inst, Natl Inst Sci Educ & Res, Sch Chem Sci, Bhubaneswar 752050, Odisha, India

Subramani, M. Siva
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OCC Homi Bhabha Natl Inst, Natl Inst Sci Educ & Res, Sch Chem Sci, Bhubaneswar 752050, Odisha, India OCC Homi Bhabha Natl Inst, Natl Inst Sci Educ & Res, Sch Chem Sci, Bhubaneswar 752050, Odisha, India

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Chandrasekhar, Vadapalli
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Tata Inst Fundamental Res Hyderabad, Hyderabad 500046, India
Indian Inst Technol Kanpur, Dept Chem, Kanpur 208016, Uttar Pradesh, India OCC Homi Bhabha Natl Inst, Natl Inst Sci Educ & Res, Sch Chem Sci, Bhubaneswar 752050, Odisha, India

Venkatasubbaiah, Krishnan
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OCC Homi Bhabha Natl Inst, Natl Inst Sci Educ & Res, Sch Chem Sci, Bhubaneswar 752050, Odisha, India OCC Homi Bhabha Natl Inst, Natl Inst Sci Educ & Res, Sch Chem Sci, Bhubaneswar 752050, Odisha, India
机构:
[1] OCC Homi Bhabha Natl Inst, Natl Inst Sci Educ & Res, Sch Chem Sci, Bhubaneswar 752050, Odisha, India
[2] Tata Inst Fundamental Res Hyderabad, Hyderabad 500046, India
[3] Indian Inst Technol Kanpur, Dept Chem, Kanpur 208016, Uttar Pradesh, India
关键词:
ONE-POT SYNTHESIS;
GENOTOXIC IMPURITIES;
METHYLATION;
1,5-DIKETONES;
ALKYLATION;
ALCOHOLS;
D O I:
10.1021/acs.joc.2c00653
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
Herein we report simple, highly efficient, and phosphine-free N,C-Ru and N,N-Ru catalysts for ligand-controlled borrowing-hydrogen (BH) and interrupted-borrowing-hydrogen (I-BH) methods, respectively. This protocol has been employed on a variety of ketones using MeOH as a green, sustainable, and alternative C1 source to form a C-C bond through the BH and I-BH methods. Reasonably good substrate scope, functional group tolerance, and good-to-excellent yields at 70 degrees C are the added highlights of these methodologies. Controlled experiments reveal that an in situ formed formaldehyde is one of the crucial elements in this ligand-controlled selective protocol, which upon reaction with a ketone generates an enone as an intermediate. This enone in the presence of the N,C-Ru catalyst and N,N-Ru catalyst through the BH and I-BH pathways yields methylated ketones and 1,5-diketones, respectively.
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页码:5135 / 5146
页数:12
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