Elsevier eBooks, Journal Year: 2023, Volume and Issue: unknown
Published: Jan. 1, 2023
Language: Английский
Nature Reviews Chemistry, Journal Year: 2024, Volume and Issue: 8(7), P. 497 - 517
Published: June 18, 2024
Language: Английский
Citations
16
Chemical Reviews, Journal Year: 2024, Volume and Issue: unknown
Published: Nov. 26, 2024
Cross-electrophile coupling (XEC), defined by us as the cross-coupling of two different σ-electrophiles that is driven catalyst reduction, has seen rapid progression in recent years. As such, this review aims to summarize field from its beginnings up until mid-2023 and provide comprehensive coverage on synthetic methods current state mechanistic understanding. Chapters are split type bond formed, which include C(sp
Language: Английский
Citations
13
Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(18), P. 2991 - 3019
Published: July 14, 2023
Abstract Propargylic alcohols are readily available bifunctional (alkyne and hydroxyl groups) synthons, which recognize as one of the attractive synthetic feedstock in organic transformations. Especially, recent years employment these valuable molecules has frequently been observed literature. Hence, present review highlights advancements application propargylic cyclization, substitution, addition reactions.
Language: Английский
Citations
15
Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(34), P. 18722 - 18730
Published: Aug. 15, 2023
Selective transformation of alkyne triple bonds to double serves as an efficient platform construct substituted alkenes. While significant advances have been made in its spatiotemporal regulation, achieving a multicomponent enantioselective reaction that requires multifaceted selectivity issues be overcome is still uncommon. Here, we report unprecedented asymmetric anti-stereoselective borylcarbofunctionalization terminal alkynes by nickel catalysis. The utilization inexpensive chiral diamine ligand enables the three-component cross-coupling alkynes, diboron reagent, and prochiral alkyl electrophiles with high levels regio-, stereo-, enantioselectivities. This provides protocol access enantioenriched alkenyl esters bearing α-stereogenic center, remarkably practical, has broad scope outstanding functional group compatibility. In addition, value this method highlighted diversity follow-up stereoretentive derivatizations stereoselective concise synthesis complex drug molecules.
Language: Английский
Citations
14
Organic Letters, Journal Year: 2023, Volume and Issue: 25(49), P. 8889 - 8894
Published: Dec. 1, 2023
A three-component 1,4-alkylarylation of 1,3-enynes with organic halides through the combination nickel and photoredox catalysis has been established, providing a novel modular approach for assembly tetrasubstituted allenes. This reductive cascade cross-electrophile reaction obviates need air-sensitive organometallic reagents stoichiometric metallic reductants. diverse range functional groups are very compatible under mild conditions give satisfactory yields. Moreover, reasonable mechanism is presented according to series control experiments.
Language: Английский
Citations
11
Chemical Science, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 1, 2025
We report a nickel-catalyzed cascade reaction leading to the arylation of an alkyne-induced acyl migration and formation all-carbon tetra-substituted alkenes in good yields with exclusive Z -selectivity.
Language: Английский
Citations
0
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(13), P. 9985 - 9992
Published: June 19, 2024
The regio- and stereoselective hydroarylation of internal alkynes via transition-metal catalysis offers a direct approach for designing highly stereodefined multifunctionalized olefins. Through recognition electronic bias, β-syn-hydroarylation poor with arylboronic acids has been well studied. However, from the same starting materials, achieving opposite α-selective anti-stereoselective remains significant challenge due to these inherent biases. Therefore, an alternative synthetic pathway trisubstituted alkenes reversed positioning configuration substituents is desirable. Based on steric repulsion-induced regioselectivity transient post-addition coordination-directed stereoselectivity, we report herein α-hydroarylation method phenylpropiolic esters using nickel catalyst that promotes formal anti-addition pathway. A broad range organoboronic acid derivatives are compatible this protocol, offering selectivity traditional reactions. distinct advantages our include precise control over selectivity, reduced loading, tolerance toward functional groups. These features highlight potential in synthesis late-stage modification alkyne-based drug intermediates, showcasing its versatility applicability organic synthesis.
Language: Английский
Citations
3
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 64(1)
Published: Nov. 7, 2024
Abstract Precise synthesis of carboxylic acids via catalytic carboxylation with CO 2 is highly appealing. Although considerable advancements have been achieved in difunctionalizing unsaturated hydrocarbons, the asymmetric variants are conspicuously underdeveloped, particularly addressing axially chiral alkenes. Herein, we report first atroposelective alkynes . A variety valuable obtained good yields and high chemo‐, regio‐, Z/E enantio‐selectivities. Notably, an unexpected anti ‐selective carbo‐carboxylation observed sp ‐hybrid carbo‐electrophile‐initiated reductive alkynes. Mechanistic studies including DFT calculation elucidate origin induction ‐selectivity vinyl‐carboxylation
Language: Английский
Citations
3
Synthesis, Journal Year: 2023, Volume and Issue: 56(12), P. 1862 - 1872
Published: Dec. 14, 2023
Abstract The construction of axially chiral alkene frameworks is currently one hottest topics in the field organic synthetic chemistry. Compared to traditional molecules, such as biaryls, heterobiaryls, and anilides, synthesis alkenes far more challenging, especially for acyclic tetrasubstituted analogues. In this review, we summarized development strategies analogues, including asymmetric difunctionalization, C–H functionalization, cross-coupling, (dynamic) kinetic resolution, allylic substitution-isomerization. 1 Introduction 2 Synthesis Cyclic Tetrasubstituted Axially Chiral Alkenes 3 Acyclic 4 Summary Outlook
Language: Английский
Citations
8
Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown
Published: Oct. 18, 2024
Abstract Axially chiral nitriles are common motifs in organic photoelectric materials, biological compounds, and agrochemicals. Unfortunately, the limited synthetic approaches to axially have impeded their availability. Herein, we report first nickel‐catalyzed desymmetric allylic cyanation of biaryl alcohols for synthesis nitrile structures high yields with excellent enantioselectivities (up 90 % yield >99 ee ). This process enables a diverse range bearing β , γ ‐unsaturated alcohol moieties. Leveraging cyano groups as versatile functionalization handles allow further derivatization these frameworks. Density functional theory (DFT) calculations suggest that both steric electronic interactions play crucial roles determining enantioselectivity this transformation. Moreover, mild facile protocol is also applicable gram‐scale preparation nitriles.
Language: Английский
Citations
1