Visible Light Induced Copper‐Catalyzed Enantioselective Deaminative Arylation of Amino Acid Derivatives Assisted by Phenol DOI
Yue Jia, Zhihan Zhang,

Guoming Yu

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(51)

Published: Nov. 8, 2023

The exploration of value-added conversions naturally abundant amino acids has received considerable attention from the synthetic community. Compared with well-established asymmetric decarboxylative transformation, deaminative transformation still remains a formidable challenge, mainly due to lack effective strategies for C-N bond activation and potential incompatibility chiral catalysts. Here, we disclose photoinduced Cu-catalyzed coupling reaction arylboronic acids. This new protocol provides series significant phenylacetamides in generally good yields excellent stereoselectivity under mild green conditions (42-85 % yields, up 97 ee). Experimental investigations theoretical calculations were performed reveal crucial role additional phenols improving catalytic efficiency enantiocontrol.

Language: Английский

Palladium-Catalyzed Thiocarbonylation of Alkenes toward Linear Thioesters DOI
Han‐Jun Ai, Fengqian Zhao, Hui‐Qing Geng

et al.

ACS Catalysis, Journal Year: 2021, Volume and Issue: 11(6), P. 3614 - 3619

Published: March 7, 2021

Thiocarbonylation of alkenes offers an ideal procedure for the synthesis thioesters. However, thiocarbonylation alkenes, especially styrenes, to produce valuable linear thioesters has remained a challenge. In this Letter, general palladium-catalyzed been achieved. Moderate good yields desired can be produced from readily available in straightforward manner.

Language: Английский

Citations

41

Nickel‐Catalyzed Enantioconvergent Carboxylation Enabled by a Chiral 2,2′‐Bipyridine Ligand DOI
Linghua Wang, Tao Li, Saima Perveen

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(51)

Published: Oct. 27, 2022

In contrast to previous approaches chiral α-aryl carboxylic acids that based on reactions using hazardous gases, pressurized setup and mostly noble metal catalysts, in this work, a nickel-catalyzed general, efficient highly enantioselective carboxylation reaction of racemic benzylic (pseudo)halides under mild conditions atmospheric CO2 has been developed. A unique 2,2'-bipyridine ligand named Me-SBpy featuring compact polycyclic skeleton enabled both high reactivity stereoselectivity. The utility method demonstrated by synthesis various (30 examples, up 95 % yield 99 : 1 er), including profen family anti-inflammatory drugs transformations the as key intermediates. Based mechanistic experimental results, plausible catalytic cycle involving Ni-complex/radical equilibrium Lewis acid-assisted activation proposed.

Language: Английский

Citations

28

Palladium-catalyzed regiodivergent hydrochlorocarbonylation of alkenes for formation of acid chlorides DOI Creative Commons

Fei Wu,

Bo Wang, Naqi Li

et al.

Nature Communications, Journal Year: 2023, Volume and Issue: 14(1)

Published: May 31, 2023

Novel strategy for acid chlorides formation that do not use carboxylic acids is particularly attractive in chemical synthesis but remains challenging. Herein, we reported the development of a highly effective Pd-catalyzed hydrochlorocarbonylation alkenes with CO alkyl chlorides. Chlorosilane and AcOH were found as mild HCl source reaction. The reaction shows broad substrate scope produces both branched linear good to high yields upon different ligands solvents. Cooperating follow-up acylation reactions, offers complementary platform diverse carbonyl compounds from alkenes. Mechanistic investigations suggested proceeded though palladium hydride pathway, prompted reductive elimination acyl-Pd-Cl intermediate.

Language: Английский

Citations

16

Palladium‐Catalyzed Enantioselective Hydrofunctionalization of Alkenes: Recent Advances DOI
Xuemei Yin, Shanshan Li, Kun Guo

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(43)

Published: Sept. 8, 2023

Abstract Palladium‐catalyzed asymmetric hydrofunctionalization of alkenes is one the most powerful and straightforward methods to forge a new C−H bond C−X (X=C, N, O, F, Si etc) bond, which provides an efficient way obtain valuable enantioenriched molecules from cheap readily available feedstocks. Catalytic simple challenging but still highly sought after. This review will mainly focus on recent advances in Palladium catalyzed over past decade, including hydroamination, hydrooxygenation, hydrofluorination, hydrosilylation, hydroarylation, hydroalkenylation hydrocarbonylation.

Language: Английский

Citations

15

Visible Light Induced Copper‐Catalyzed Enantioselective Deaminative Arylation of Amino Acid Derivatives Assisted by Phenol DOI
Yue Jia, Zhihan Zhang,

Guoming Yu

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(51)

Published: Nov. 8, 2023

The exploration of value-added conversions naturally abundant amino acids has received considerable attention from the synthetic community. Compared with well-established asymmetric decarboxylative transformation, deaminative transformation still remains a formidable challenge, mainly due to lack effective strategies for C-N bond activation and potential incompatibility chiral catalysts. Here, we disclose photoinduced Cu-catalyzed coupling reaction arylboronic acids. This new protocol provides series significant phenylacetamides in generally good yields excellent stereoselectivity under mild green conditions (42-85 % yields, up 97 ee). Experimental investigations theoretical calculations were performed reveal crucial role additional phenols improving catalytic efficiency enantiocontrol.

Language: Английский

Citations

15