Rhodium(III)-catalyzed [3+2] annulative coupling between oximes and electron-deficient alkynes

Zhou, Xukai; Yu, Songjie; Qi, Zisong; Li, Xingwei

doi:10.1007/s11426-015-5408-8

Cited by 25 publications

(15 citation statements)

References 50 publications

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“…164 Here the use of electron-deficient alkynes was crucial for achieving good yields, and reactions proceeded with high regioselectivity to give the regioisomer shown. A variety of substituents were also tolerated on the aryl ring of the O -methoxy oxime.…”

Section: Additions To C=c π-Bonds Followed By Cyclization Upon Pomentioning

confidence: 99%

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

2016

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The transition metal-catalyzed addition of C–H bonds to carbonyls, imines and related polarized π-bonds has emerged as a particularly efficient and powerful approach for the construction of an incredibly diverse array of heteroatom substituted products. Readily available and stable inputs are typically employed, and reactions often proceed with very high functionality group compatibility and without the production of waste byproducts. Additionally, many transition metal-catalyzed C–H bond additions to polarized π-bonds occur within cascade reaction sequences to provide rapid access to a diverse array of different heterocyclic as well as carbocyclic products. This review highlights the diversity of transformations that have been achieved, catalysts that have been used, and types of products that have been prepared through the transition metal catalyzed addition of C–H bonds to carbonyls, imines and related polarized π-bonds.

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Section: Additions To C=c π-Bonds Followed By Cyclization Upon Pomentioning

confidence: 99%

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

2016

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“…(3)]. Around the same time, Li and co‐workers demonstrated that trifluoromethanesulfonyl alkynes could be applied in rhodium‐catalyzed [3+2] annulation with O ‐methyl oximes to afford amino indene products 229 [Eq. (4)].…”

Section: N‐substituted Quaternary Centersmentioning

confidence: 99%

Transition‐Metal‐Catalyzed C−H Functionalization for Construction of Quaternary Carbon Centers

2018

Chemistry A European J

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Efficient construction of quaternary carbon centers represents one of the most challenging goals in organic synthesis, and it has drawn tremendous research interest from organic chemist community. The past decade has witnessed a significant advancement of direct C-H functionalization, which delivers various synthetic tools for assembling structurally diversified architectures with the advantage of step- and atom-economy, operational simplicity, and readily available substrates. In this Minireview, synthetic methods based on transition-metal-catalyzed C-H functionalization as efficient tools for the construction of quaternary carbon centers are summarized.

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“…[ 1,2 ] Rhodium‐catalyzed CH functionalization has become an effective method to synthesize these compounds. [ 3–5 ] To ensure high selectivity for the CH bond activation in these reactions, [ 6–11 ] the directing groups are accommodated widely. [ 12–14 ]…”

Section: Introductionmentioning

confidence: 99%

Theoretical investigation on the rhodium‐catalyzed coupling reaction of ketoxime with 1,3‐enynes: [4 + 1] vs [4 + 2] annulation

Yun

Liu

2020

Int J of Quantum Chemistry

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The mechanisms of rhodium‐catalyzed coupling reaction of ketoxime and 1,3‐enynes were investigated by using density functional theory calculations. Different 1,3‐enynes would lead to different annulation products. Reaction A undergoes five sequential steps (CH activation, 1,3‐enyne migratory insertion, 1,4‐Rh migration, cyclization, and deprotonation) to lead to the [4 + 1] annulation product, whereas due to the electronic effect, the process generating the [4 + 2] product in reaction A is restricted. In contrast, the electron‐withdrawing group of the N(Me)2 group in 1,3‐enyne would bring about the [4 + 2] annulation product in reaction B. Our calculated results indicate that no [4 + 1] annulation product could be obtained in reaction C, in agreement with the experimental observation that the cis‐allyl hydrogen in 1,3‐enyne is crucial for the [4 + 1] annulation reaction.

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Rhodium(III)-catalyzed [3+2] annulative coupling between oximes and electron-deficient alkynes

Cited by 25 publications

References 50 publications

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

Transition‐Metal‐Catalyzed C−H Functionalization for Construction of Quaternary Carbon Centers

Theoretical investigation on the rhodium‐catalyzed coupling reaction of ketoxime with 1,3‐enynes: [4 + 1] vs [4 + 2] annulation

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