Divergent and Selective Light Alkene Cross‐Coupling DOI

Zi‐Chao Wang,

Jiawen Zhang, Ming Joo Koh

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(45)

Опубликована: Окт. 2, 2023

Light olefins are abundantly manufactured in the petroleum industry and thus represent ideal starting materials for modern chemical synthesis. Selective divergent transformations of feedstock light to value-added chemicals highly sought-after but remain challenging. Herein we report an exceptionally regioselective carbonickelation alkenes followed by situ trapping with three types nucleophiles, namely a reductant, base, or Grignard reagent. This protocol enables efficient 1,2-hydrofunctionalization, dicarbofunctionalization, branched-selective Heck-type cross-coupling aryl alkenyl reagents streamline access diverse alkyl arenes complex alkenes. Harnessing bulky N-heterocyclic carbene ligands acenaphthyl backbones nickel catalysts is crucial attain high reactivity selectivity. strategy provides rare, modular, platform upgrading expected find broad applications medicinal chemistry industrial processes.

Язык: Английский

Nickel-catalyzed Heck reaction of cycloalkenes using aryl sulfonates and pivalates DOI
Jianrong Steve Zhou, Xiaolei Huang, Shenghan Teng

и другие.

Chemical Communications, Год журнала: 2021, Номер 57(32), С. 3933 - 3936

Опубликована: Янв. 1, 2021

Nickel-catalyzed Heck reaction of cycloalkenes produces uncommon isomers with aryl rings in conjugation olefins.

Язык: Английский

Процитировано

15

Acid/Base-Tuned Asymmetric Reductive Heck and Denitrogenative Heck Reactions of In Situ-Formed α,β-Unsaturated Hydrazone DOI

Shuling Yu,

Xiaoyu Zhou, Xiaofeng Tong

и другие.

ACS Catalysis, Год журнала: 2024, Номер 15(1), С. 72 - 80

Опубликована: Дек. 13, 2024

Despite significant progress in the catalytic asymmetric 1,4-additions between various Michael donors and acceptors, exploration of organohalide remains elusive. Herein, we report Pd(0)-catalyzed intramolecular vinyl/aryl iodides to α,β-unsaturated hydrazones, featuring situ-formed hydrazone acid/base-tuned reaction pathways. Due its strong coordination ability, is capable steering C–C bond formation follow 1,4-addition mechanism instead conventional alkene insertion, thus enabling generation vinylhydrazinyl–Pd2+ species via Zimmerman–Traxler chairlike transition state. Notably, this preferentially undergoes protonation under acidic conditions, furnishing a reductive Heck with aid native hydrazine reductant, while it susceptible β-HN elimination basic conditions achieve denitrogenative reaction. The protocol affords highly enantioselective access diverse heterocycles, groups poised for further chemical manipulations.

Язык: Английский

Процитировано

2

Nickel-Catalyzed Reductive Cascade Arylalkylation of Alkenes with Alkylpyridinium Salts DOI

Jun Jin Yang,

Lina Yang,

Jing Gu

и другие.

Organic Letters, Год журнала: 2022, Номер 24(12), С. 2376 - 2380

Опубликована: Март 23, 2022

Herein, we describe a nickel-catalyzed reductive deaminative arylalkylation of tethered alkenes with pyridinium salts as C(sp3) electrophiles. This two-component dicarbofunctionalization reaction enables the efficient synthesis various benzene-fused cyclic compounds bearing all-carbon quaternary centers. The approach presented in this paper proceeds under mild conditions, tolerating wide variety functional groups and heterocycles. It has been used to functionalize complicated molecules at late stage.

Язык: Английский

Процитировано

9

Carbon Nanotubes in Organic Catalysis DOI
Angel Luis Corcho‐Valdés, Claudia Iriarte‐Mesa,

Jesús Calzadilla-Maya

и другие.

Composites science and technology, Год журнала: 2022, Номер unknown, С. 223 - 266

Опубликована: Янв. 1, 2022

Nanoscience and nanotechnology have revolutionized organic catalysis, increasing the efficiency of these reactions reducing their environmental impact. Particularly, carbon nanotubes are widely used in many such as C–C couplings, hydrogenations, alkane dehydrogenations, transesterifications oxidations. Excellent results been obtained terms synthesis catalysts, reaction yields, selectivity, reusability. In this review, we provide a general overview design, synthesis, use catalysts catalytic supports, along with main strategies for surface functionalization doping heteroatoms. Concluding considerations from authors' perspective provided, regarding promising materials challenges to be faced near future.

Язык: Английский

Процитировано

9

Divergent and Selective Light Alkene Cross‐Coupling DOI

Zi‐Chao Wang,

Jiawen Zhang, Ming Joo Koh

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(45)

Опубликована: Окт. 2, 2023

Light olefins are abundantly manufactured in the petroleum industry and thus represent ideal starting materials for modern chemical synthesis. Selective divergent transformations of feedstock light to value-added chemicals highly sought-after but remain challenging. Herein we report an exceptionally regioselective carbonickelation alkenes followed by situ trapping with three types nucleophiles, namely a reductant, base, or Grignard reagent. This protocol enables efficient 1,2-hydrofunctionalization, dicarbofunctionalization, branched-selective Heck-type cross-coupling aryl alkenyl reagents streamline access diverse alkyl arenes complex alkenes. Harnessing bulky N-heterocyclic carbene ligands acenaphthyl backbones nickel catalysts is crucial attain high reactivity selectivity. strategy provides rare, modular, platform upgrading expected find broad applications medicinal chemistry industrial processes.

Язык: Английский

Процитировано

5