Towards the Development of Frustrated Lewis Pair (FLP) Catalyzed Hydrogenations of Tertiary and Secondary Carboxylic Amides DOI
Jan Paradies,

Laura Köring,

Nikolai A. Sitte

et al.

Synthesis, Journal Year: 2021, Volume and Issue: 54(05), P. 1287 - 1300

Published: Oct. 28, 2021

Abstract The development of the frustrated Lewis pair catalyzed hydrogenation tertiary and secondary amides is reviewed. Detailed insight into our strategies in order to overcome challenges during reaction process provided. Furthermore, developed chemistry extended polyamides trifluoroacetamides for convenient introduction trifluoroethyl groups organic molecules.

Language: Английский

Diverse Uses of the Reaction of Frustrated Lewis Pair (FLP) with Hydrogen DOI
Douglas W. Stephan

Journal of the American Chemical Society, Journal Year: 2021, Volume and Issue: 143(48), P. 20002 - 20014

Published: Nov. 17, 2021

The articulation of the notion "frustrated Lewis pairs" (FLPs) emerged from discovery that H2 can be reversibly activated by combinations sterically encumbered main group acids and bases. This has prompted numerous studies focused on various perturbations acid/base applications to organic reductions. Perspective focuses new directions developments are emerging this FLP chemistry involving hydrogen. Three areas discussed including approaches reductions, reductions small molecules, advances in heterogeneous systems. These foci serve illustrate despite having its roots chemistry, simple concept FLPs is being applied across discipline.

Language: Английский

Citations

194
Frustrated Lewis pair chemistry of alkynes DOI
Jing Guo, Maying Yan, Douglas W. Stephan

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(8), P. 2375 - 2396

Published: Jan. 1, 2024

This review is focused on the chemistry of frustrated Lewis pairs (FLPs) with alkynes and surveys range stoichiometric catalytic reactions enabled by this concept.

Language: Английский

Citations

8
Acid-catalyzed conversion of sesamolin to sesamol: Kinetics and reaction mechanism based on density functional theory DOI

Ling-Shuai Liu,

Yu-meng Yu,

Chenxia Zhang

et al.

Food Chemistry, Journal Year: 2025, Volume and Issue: 472, P. 142972 - 142972

Published: Jan. 20, 2025

Language: Английский

Citations

1
Asymmetric Reduction of Quinolines: A Competition between Enantioselective Transfer Hydrogenation and Racemic Borane Catalysis DOI

Bochao Gao,

Zaiqi Han, Wei Meng

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(5), P. 3335 - 3339

Published: Feb. 17, 2023

A chiral phosphoric acid catalyzed asymmetric transfer hydrogenation of quinolines with regenerable dihydrophenanthridine derived by a borane-catalyzed phenanthridine under H2 has been successfully realized. Despite the competition racemic pathway, variety tetrahydroquinolines were furnished in high yields up to 91% ee.

Language: Английский

Citations

13
Origin of Stereoselectivity in FLP-Catalyzed Asymmetric Hydrogenation of Imines DOI Creative Commons
Andrea Hamza, Kristina Sorochkina,

Bianka Kótai

et al.

ACS Catalysis, Journal Year: 2020, Volume and Issue: 10(23), P. 14290 - 14301

Published: Nov. 23, 2020

Development of metal-free strategies for stereoselective hydrogenation unsaturated substrates is particular interest in asymmetric synthesis. The emerging chemistry frustrated Lewis pairs offers a promising approach along this line as demonstrated by recent achievements. However, the stereocontrol elements these reactions are not clearly recognized thus far. Herein, we analyze origin stereoinduction direct imines catalyzed set chiral boranes. We use tools computational to describe elementary steps catalytic cycle, and pay special attention stereoselectivity-determining hydride transfer process. enantioselectivities predicted applied very good agreement with previous experimental observations. find that stereoselectivity governed thermodynamically less favored conformer borohydride intermediate experimentally observed form. most transition states stabilized specific aryl–aryl alkyl–aryl noncovalent interactions, which play an important role stereoinduction. This insight exploited proposing additional borane variants improve enantioselectivity, could be

Language: Английский

Citations

31
Recent Advances in Asymmetric Catalysis Using p‐Block Elements DOI Creative Commons
Milan Pramanik, Michael G. Guerzoni, Emma Richards

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(9)

Published: Dec. 1, 2023

The development of new methods for enantioselective reactions that generate stereogenic centres within molecules are a cornerstone organic synthesis. Typically, metal catalysts bearing chiral ligands as well organocatalysts have been employed the synthesis compounds. In this review, we highlight recent advances in main group catalysis using p-block elements (boron, aluminium, phosphorus, bismuth) complementary and sustainable approach to molecules. Several these benefit terms high abundance, low toxicity, selectivity, excellent reactivity. This minireview summarises utilisation element asymmetric value-added

Language: Английский

Citations

11
B(C6F5)3-Catalyzed site-selective N1-alkylation of benzotriazoles with diazoalkanes DOI
Yunbo Zhao, Dipendu Mandal, Jing Guo

et al.

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(63), P. 7758 - 7761

Published: Jan. 1, 2021

The site-selective N1-alkylation of benzotriazoles with diazoalkanes is achieved using 10 mol% B(C6F5)3 as a catalyst.

Language: Английский

Citations

23
FLP-CO2 adducts: Convenient sources of frustrated Lewis pairs for stoichiometric and catalytic chemistry DOI Creative Commons

Jordan W. Thomson,

Marc‐André Courtemanche,

R.C. Neu

et al.

Dalton Transactions, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

[ t Bu 3 PCO 2 B(C 6 F 5 ) ] 1 and [TMPH][C H Me 4 NCO 7 act as FLP precursors react with , disulfides, alkynes, silanes phenols. While is a catalyst precursor for the hydrogenation hydrosilylation of selected substrates.

Language: Английский

Citations

0
Rare-earth mediated dihydrogen activation and catalytic hydrogenation DOI

Yiwen Guan,

Erli Lu, Xin Xu

et al.

Journal of Rare Earths, Journal Year: 2021, Volume and Issue: 39(9), P. 1017 - 1023

Published: Jan. 9, 2021

Language: Английский

Citations

19
Chiral Dienes: From Ligands to FLP Catalysts DOI
Xiangqing Feng, Wei Meng, Haifeng Du

et al.

Chinese Journal of Chemistry, Journal Year: 2021, Volume and Issue: 40(9), P. 1109 - 1116

Published: Dec. 27, 2021

Comprehensive Summary Olefins are very easily accessible compounds which both popular substrates in synthetic chemistry and good ligands the organometallic complexes. This dual character makes olefins a rich source of chiral catalysts for asymmetric catalysis. Herein, we will briefly summarize our studies on development diene transition‐metal catalyzed reactions FLP metal‐free hydrogenations hydrosilylations. Several acyclic as well P/olefin S/olefin hybrid were developed Rh or Pd‐catalyzed reactions. With these hand, further put forward novel strategy acquiring via situ hydroboration dienes with Piers’ borane. These proved to be highly effective hydrosilylations imines, silyl enol ethers, ketones, aromatic N ‐heterocycles. What is most favorite original your research group? The precursors catalysts. How do you get into this specific field? Could please share some experiences readers? When I started my independent 2008, belong one ligand type. We got field thought simpler better. experience led us step important personality scientific research? Courage persistence doing something unique. hobbies? Walking playing cards. keep balance between family? Life not only research, but also family. You believe it, there. journal(s)? My journal Organic Letters , authors can publish their work rapidly readers browse progress organic comprehensively.

Language: Английский

Citations

16