Bu<sub>3</sub>SnH-Catalyzed Reduction of Nitroalkanes to Alkanes

Tormo, Jordi; Hays, David S.; Fu, Gregory C.

doi:10.1021/jo980789k

Cited by 78 publications

(24 citation statements)

References 15 publications

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“…The hydrosilylation of aromatic nitro compounds has been less explored as compared to hydrosilylation of carbonyl derivatives . The hydrosilylation of nitro compounds have been studied using transition metal catalyst such as Pd, Pt, Rh, Sn, and Re catalysts …”

Section: Hydrosilylation Of Nitroarenesmentioning

confidence: 99%

Sustainable Amine Synthesis: Iron Catalyzed Reactions of Hydrosilanes with Imines, Amides, Nitroarenes and Nitriles

Shaikh¹

2019

ChemistrySelect

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Iron catalyzed organic synthesis has emerged as a sustainable chemistry due to the highly competitive cost, high natural abundance and ecologically acceptable properties of iron. Moreover, its extensive range of oxidation states i. e. -II to + VI provides numerous opportunities to perform multiple organic reactions. Recently iron catalysis has started competing the established precious metals. Among organic scaffolds, amines are important building blocks that are useful in the various fields starting from drugs, crop protection chemicals to dyes and pigments. Typically, hydrogenation or reduction of functional groups such as imines, amides, nitroarenes and nitriles results into amines. In this context, homogeneous iron catalyzed hydrosilylation is a highly promising alternative to traditional hydrogenation and other reduction reactions. This review is focused on the synthesis of amine and its derivatives via hydrosilylation of imines, amides, nitroarenes and nitriles using iron as a catalyst. Some of the reduction methods of these functional groups that may not follow the typical hydrosilylation pathway are also included in this review due to their strong relevance to the theme. The phenomenal progress in this focused area is summarized to witness this transformation towards sustainable development in the field of amine synthesis.

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Section: Hydrosilylation Of Nitroarenesmentioning

confidence: 99%

Sustainable Amine Synthesis: Iron Catalyzed Reactions of Hydrosilanes with Imines, Amides, Nitroarenes and Nitriles

Shaikh¹

2019

ChemistrySelect

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“…548 Tertiary nitro alkanes or activated nitro groups are reduced to the alkane with loss of the nitro group by a combination of PhSiH 3 and catalytic amounts of (n-Bu) 3 SnH and 1,1 -azobis(cyclohexanecarbonitrile) (ACHN), even in the presence of other potentially reducible functional groups. 555 The examples shown in Eqs. 331 …”

Section: Reduction Of Oximesmentioning

confidence: 99%

Ionic and Organometallic‐Catalyzed Organosilane Reductions

2009

Ionic and Organometallic‐Catalyzed Organosilane Reductions

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“…In general, these methods suffer from the use of unsavoury reagents (for example, MeSNa, NaTeH, n Bu 3 SnH, or SnCl 4 ) in stoichiometric quantities and from limitations in their scope. Conditions have been reported which involve the use of 10 mol % n ‐Bu 3 SnH and PhSiH 3 (0.5 equiv), however, the substrates reported contain tertiary nitroalkanes, with 2‐nitromalonate as the sole exception 4. On exposure of benzylic (or allylic) and tertiary nitroalkanes to Pd/H 2 , the N ‐benzylamines have been the desired end products, and CNO 2 bond cleavage, when observed, deemed an undesirable side reaction 5.…”

Section: Study Into the Effects Of Solvent And Temperaturementioning

confidence: 99%

Pd‐Catalyzed Cleavage of Benzylic Nitro Bonds: New Opportunities for Asymmetric Synthesis

Motoyoshi

Carreira

2007

Angewandte Chemie

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Spurlos verschwunden: Benzylische Nitroalkane werden in guten Ausbeuten mit einem einfachen Verfahren, das eine heterolytische C‐N‐Bindungsspaltung umfasst, zu den entsprechenden Alkanen reduziert (siehe Schema). Die spurlose Entfernung der Nitrogruppe lässt ein stereogenes Zentrum zurück, das auf anderem Weg schwierig zu erzeugen sein könnte. Die Reaktion erweitert somit die Bandbreite an zugänglichen Synthesebausteinen.

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Bu₃SnH-Catalyzed Reduction of Nitroalkanes to Alkanes

Cited by 78 publications

References 15 publications

Sustainable Amine Synthesis: Iron Catalyzed Reactions of Hydrosilanes with Imines, Amides, Nitroarenes and Nitriles

Sustainable Amine Synthesis: Iron Catalyzed Reactions of Hydrosilanes with Imines, Amides, Nitroarenes and Nitriles

Ionic and Organometallic‐Catalyzed Organosilane Reductions

Pd‐Catalyzed Cleavage of Benzylic Nitro Bonds: New Opportunities for Asymmetric Synthesis

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Bu3SnH-Catalyzed Reduction of Nitroalkanes to Alkanes

Cited by 78 publications

References 15 publications

Sustainable Amine Synthesis: Iron Catalyzed Reactions of Hydrosilanes with Imines, Amides, Nitroarenes and Nitriles

Sustainable Amine Synthesis: Iron Catalyzed Reactions of Hydrosilanes with Imines, Amides, Nitroarenes and Nitriles

Ionic and Organometallic‐Catalyzed Organosilane Reductions

Pd‐Catalyzed Cleavage of Benzylic Nitro Bonds: New Opportunities for Asymmetric Synthesis

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Bu₃SnH-Catalyzed Reduction of Nitroalkanes to Alkanes