Nickel-Catalyzed Reductive Cross-Coupling of Unactivated Alkyl Halides

Yu, Xiaolong; Yang, Tao; Wang, Shulin; Xu, Hailiang; Gong, Hegui

doi:10.1021/ol200617f

Cited by 231 publications

(104 citation statements)

References 42 publications

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“…The ligands X-pybox (X = H [23], Cl [28], Ph [29], and CH 3 O [30]) were prepared according to the known procedure. A new derivative CH 3 S-pybox was prepared according to the known procedure for the CH 3 O-pybox [30] with modification.…”

Section: Methodsmentioning

confidence: 99%

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Pybox-Iron(II) Spin-Crossover Complexes with Substituent Effects from the 4-Position of the Pyridine Ring (Pybox = 2,6-Bis(oxazolin-2-yl)pyridine)

Kimura

Ishida

2017

Inorganics

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Spin-crossover (SCO) behavior of a series of [Fe(X-pybox) 2 ](ClO 4 ) 2 was investigated, where X-pybox stands for 4-X-substituted 2,6-bis(oxazolin-2-yl)pyridine with X = H, Cl, Ph, CH 3 O, and CH 3 S. We confirmed that the mother compound [Fe(H-pybox) 2 ](ClO 4 ) 2 underwent SCO above room temperature. After X was introduced, the SCO temperatures (T 1/2 ) were modulated as 310, 230, and 330 K for X = Cl, Ph, and CH 3 S, respectively. The CH 3 O derivative possessed the high-spin state down to 2 K. Crystallographic analysis for X = H, Cl, CH 3 O, and CH 3 S was successful, being consistent with the results of the magnetic study. Distorted coordination structures stabilize the HS (high-spin) state, and the highest degree of the coordination structure distortion is found in the CH 3 O derivative. A plot of T 1/2 against the Hammett substituent constant σ p showed a positive relation. Solution susceptometry was also performed to remove intermolecular interaction and rigid crystal lattice effects, and the T 1/2 's were determined as 260, 270, 240, 170, and 210 K for X = H, Cl, Ph, CH 3 O, and CH 3 S, respectively, in acetone. The substituent effect on T 1/2 became very distinct, and it is clarified that electron-donating groups stabilize the HS state.

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Section: Methodsmentioning

confidence: 99%

“…New compounds [Fe(X-pybox)2](ClO4)2 (X = Cl, Ph, CH3O, CH3S) were prepared according to the conventional method [23,[28][29][30]. All the ligands were known, except for X = CH3S.…”

Section: Preparationmentioning

confidence: 99%

Pybox-Iron(II) Spin-Crossover Complexes with Substituent Effects from the 4-Position of the Pyridine Ring (Pybox = 2,6-Bis(oxazolin-2-yl)pyridine)

Kimura

Ishida

2017

Inorganics

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“…It may also bind to the catalytic species in a cage upon its generation via one-electron reduction or halide abstraction by low-valent Ni (cage-rebound, Scheme 2) [21][22][23]. While radicalchain mechanisms may operate for construction of C(sp 3 )-C(sp 2 ) bonds, (for reviews on Ni-catalyzed conventional coupling chemistry, see [9][10][11][12][13][14][15]) formation of C(sp 3 )-C(sp 3 ) bonds via a cage-rebound process is possible according to previous studies on the Ni-catalyzed Negishi chemistry (Scheme 2) [23].…”

Section: )-Ni II ] Intermediate Via a Radical-chain Process (Scheme 2mentioning

confidence: 99%

“…While radicalchain mechanisms may operate for construction of C(sp 3 )-C(sp 2 ) bonds, (for reviews on Ni-catalyzed conventional coupling chemistry, see [9][10][11][12][13][14][15]) formation of C(sp 3 )-C(sp 3 ) bonds via a cage-rebound process is possible according to previous studies on the Ni-catalyzed Negishi chemistry (Scheme 2) [23]. The latter transformation, however, is much less understood [21].…”

Section: )-Ni II ] Intermediate Via a Radical-chain Process (Scheme 2mentioning

confidence: 99%

Nickel-Catalyzed Reductive Couplings

2016

Self Cite

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The Ni-catalyzed reductive coupling of alkyl/aryl with other electrophiles has evolved to be an important protocol for the construction of C-C bonds. This chapter first emphasizes the recent progress on the Ni-catalyzed alkylation, arylation/vinylation, and acylation of alkyl electrophiles. A brief overview of CO2 fixation is also addressed. The chemoselectivity between the electrophiles and the reactivity of the alkyl substrates will be detailed on the basis of different Ni-catalyzed conditions and mechanistic perspective. The asymmetric formation of C(sp(3))-C(sp(2)) bonds arising from activated alkyl halides is next depicted followed by allylic carbonylation. Finally, the coupling of aryl halides with other C(sp(2))-electrophiles is detailed at the end of this chapter.

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“…However, a Negishi process can not be ruled out when alkyl iodides are employed as the coupling partners. [46] Scheme 14. Nickel-catalyzed reductive coupling of alkyl halides.…”

Section: Negishi Reactionsmentioning

confidence: 99%

Nickel‐Catalyzed Cross‐Coupling with Pincer Ligands

Wang

Liu

2012

Eur J Inorg Chem

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Transition‐metal‐catalyzed cross‐coupling reactions are powerful tools for constructing carbon–carbon and carbon–heteroatom bonds. In this microreview we summarize the nickel‐catalyzed cross‐coupling reactions with pincer ligands. The reactions presented here include Kumada, Negishi, Suzuki, and Sonogashira reactions for the formation of different types of C–C bonds, as well as the thiolation of aryl iodides.

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Nickel-Catalyzed Reductive Cross-Coupling of Unactivated Alkyl Halides

Cited by 231 publications

References 42 publications

Pybox-Iron(II) Spin-Crossover Complexes with Substituent Effects from the 4-Position of the Pyridine Ring (Pybox = 2,6-Bis(oxazolin-2-yl)pyridine)

Pybox-Iron(II) Spin-Crossover Complexes with Substituent Effects from the 4-Position of the Pyridine Ring (Pybox = 2,6-Bis(oxazolin-2-yl)pyridine)

Nickel-Catalyzed Reductive Couplings

Nickel‐Catalyzed Cross‐Coupling with Pincer Ligands

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