Nickel‐Catalyzed Reductive Amidation of Unactivated Alkyl Bromides

Serrano, Eloisa; Martı́n, Rubén

doi:10.1002/ange.201605162

Cited by 17 publications

(2 citation statements)

References 69 publications

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“…However, reactions using carbamoyl chlorides turned out to be unsuccessful. To our delight, isocyanates [58][59][60] proved to be a competitive electrophilic carbamoylating agent in our catalytic system under slightly modified conditions. The scope of this asymmetric aryl-carbamoylation reaction was explored, and the results were summarized in Table 4.…”

Section: Scope Of Tethered Alkenesmentioning

confidence: 91%

Nickel-Catalyzed Reductive Asymmetric Aryl-Acylation and Aryl-Carbamoylation of Unactivated Alkenes

2022

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Herein we reported a nickel-catalyzed asymmetric two-component reductive aryl-acylation and arylcarbamoylation of aryl iodide-tethered unactivated alkenes, which utilize ortho-pyridinyl esters and isocyanates as the electrophilic acyl sources, respectively. Under the catalysis of a nickel-Pyrox complex with zinc powder as the reductant, a variety of chiral indanes, indolines, and dihydrobenzofurans bearing a quaternary stereogenic center were prepared in moderate to high efficiency and good to excellent enantioselectivities. The utility of this method is demonstrated by various simple derivatizations of the attached carbonyl group, particularly the sequential benzylic oxidation and pinacol coupling, which provides a concise entry to benzene-fused bicyclic bridged ring framework containing three challenging tetrasubstituted stereocenters in high stereocontrol.

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Section: Scope Of Tethered Alkenesmentioning

confidence: 91%

Nickel-Catalyzed Reductive Asymmetric Aryl-Acylation and Aryl-Carbamoylation of Unactivated Alkenes

2022

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“…[30][31][32] Other selective couplings of alkyl organonickel nucleophiles derived from alkyl halides have been described by Martin, and their use has been focused thus far to trapping with electrophiles such as CO2 and isocyanates. [33][34][35][36] Table 1. Optimization of Reaction Parameters.…”

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confidence: 99%

Nickel-Catalyzed Reductive Coupling of Unactivated Alkyl Bromides and Aliphatic Aldehydes

Cruz¹,

Montgomery

2021

Preprint

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We report the development of a mild, convenient coupling of aliphatic aldehydes and unactivated alkyl bromides. The catalytic system features the use of a common Ni(II) precatalyst and a readily available bisoxazoline ligand and affords silyl-protected secondary alcohols. The reaction is operationally simple, utilizing Mn as a stoichiometric reductant, and tolerates a wide range of functional groups. Initial mechanistic experiments support a mechanism featuring an alpha-silyloxy Ni species which undergoes formal oxidative addition of the alkyl bromide species via a reductive cross-coupling pathway.

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Zirconium/Nickel‐Mediated One‐Pot Ketone Synthesis

Kishi

Ai²,

Ye³

et al. 2017

Angewandte Chemie

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A zirconium/nickel‐mediated one‐pot synthesis of ketones is reported. In the presence of Zn or Mn, Cp2ZrCl2 was found to dramatically accelerate the coupling and suppress side product formation via an I→SPy displacement at the same time. Unlike Zn/Pd‐ and Fe/Cu‐mediated one‐pot ketone syntheses, the new method is effective for nucleophiles bearing OR or equivalent functional groups at the α‐position. A mechanism comprising a nickel catalytic cycle, a zirconium catalytic cycle, and Zr→Ni transmetalation is proposed, and Cp2ZrCl2 and/or low‐valent Zr species are suggested to play crucial dual roles.

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Nickel‐Catalyzed Reductive Amidation of Unactivated Alkyl Bromides

Cited by 17 publications

References 69 publications

Nickel-Catalyzed Reductive Asymmetric Aryl-Acylation and Aryl-Carbamoylation of Unactivated Alkenes

Nickel-Catalyzed Reductive Asymmetric Aryl-Acylation and Aryl-Carbamoylation of Unactivated Alkenes

Nickel-Catalyzed Reductive Coupling of Unactivated Alkyl Bromides and Aliphatic Aldehydes

Zirconium/Nickel‐Mediated One‐Pot Ketone Synthesis

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