Enantioselective Hydrophosphination of Terminal Alkenyl Aza‐Heteroarenes DOI Creative Commons
Esther G. Sinnema, Tizian‐Frank Ramspoth, Reinder H. Bouma

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 136(7)

Published: Dec. 22, 2023

Abstract This paper presents a Mn(I)‐catalysed methodology for the enantioselective hydrophosphination of terminal alkenyl aza‐heteroarenes. The catalyst operates through H−P bond activation, enabling successful diverse range alkenyl‐heteroarenes with high enantioselectivity. presented protocol addresses inherently low reactivity and commonly encountered suboptimal enantioselectivities these challenging substrates. As an important application we show that this method facilitates synthesis non‐symmetric tridentate P,N,P‐containing ligand like structure in just two synthetic steps using single catalytic system.

Language: Английский

gem-Difluoroallene (DFA): An Emerging Versatile Synthetic Precursor to Enable Diverse Fluorinated Molecules DOI
Kota Sathish, Swati Jain, Naveen Sihag

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Organofluorine compounds are increasingly found in diverse fields, such as pharmaceuticals, agrochemicals, and materials science.

Language: Английский

Citations

3
Enantioselective Hydrophosphination of Terminal Alkenyl Aza‐Heteroarenes DOI Creative Commons
Esther G. Sinnema, Tizian‐Frank Ramspoth, Reinder H. Bouma

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(7)

Published: Dec. 22, 2023

Abstract This paper presents a Mn(I)‐catalysed methodology for the enantioselective hydrophosphination of terminal alkenyl aza‐heteroarenes. The catalyst operates through H−P bond activation, enabling successful diverse range alkenyl‐heteroarenes with high enantioselectivity. presented protocol addresses inherently low reactivity and commonly encountered suboptimal enantioselectivities these challenging substrates. As an important application we show that this method facilitates synthesis non‐symmetric tridentate P,N,P‐containing ligand like structure in just two synthetic steps using single catalytic system.

Language: Английский

Citations

8
Copper-Catalyzed Protoarylation of gem-Difluoroallenes DOI
Wei Li, Cheng Wang,

Mengdie Xiao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(2), P. 525 - 529

Published: Jan. 5, 2024

A copper-catalyzed protoarylation of gem-difluoroallenes with aryl boronic esters has been developed, enabling highly regioselective synthesis gem-difluoroalkenes in high yields. The mild reaction conditions allow for a variety functional groups to be tolerated, and the can extended protoalkenylation gem-difluoroallenes. synthetic utility this method demonstrated gram-scale operation as well chiral bearing γ-carbon stereogenic centers moderate enantioselectivity using bidentate phosphine ligand copper catalyst.

Language: Английский

Citations

2
Cobalt- or rhodium-catalyzed synthesis of 1,2-dihydrophosphete oxides via C–H activation and formal phosphoryl migration DOI Creative Commons
Shengbo Xu,

Ruijie Mi,

Guangfan Zheng

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(16), P. 6012 - 6021

Published: Jan. 1, 2024

A highly stereo- and chemoselective intermolecular coupling of diverse heterocycles with dialkynylphosphine oxides has been realized

Language: Английский

Citations

2
Diastereoselective and Enantioselective Hydrophosphinylations of Conjugated Enynes, Allenes and Dienes via Synergistic Pd/Co Catalysis DOI

Minhao Tang,

Zhen‐Yu Yang, Aijun Han

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 137(1)

Published: Sept. 10, 2024

Abstract Different from the reported work focusing on construction of single P ‐ or C ‐stereocenter via hydrophosphinylation unsaturated carbon bonds, highly diastereo‐ and enantioselective reaction allenes, conjugated enynes 1,3‐dienes is achieved a designed Pd/Co dual catalysis newly modified masked phosphinylating reagent. A series allyl motifs bearing both tertiary are prepared in generally good yields, >20 : 1 dr, rr 99 % ee. The unprecedented 1,3‐enynes established to generate skeletons containing nonadjacent chiral axis. first stereodivergent also developed achieve all four ‐containing stereoisomers. present protocol features use only 3‐minutes time 0.1 catalyst, with observation up 730 TON. set mechanistic studies reveal necessity roles two metal catalysts corroborate synergistic process.

Language: Английский

Citations

1
Z-Selective access to α-trifluoromethyl arylenes through Pd-catalysed fluoroarylation of 1,1-difluoroallenes DOI
Lei Chen,

Ze-Feng Luo,

Peng Ye

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(45), P. 8979 - 8983

Published: Jan. 1, 2023

The synthesis of stereo-defined α-trifluoromethyl arylenes is great importance in medical chemistry, organic and materials science. However, despite the recent advances, Z-selective formation has remained underdeveloped. Here, we describe a facile approach towards Z-α-trifluoromethyl through Pd-catalysed stereoselective fluoroarylation 1,1-difluoroallenes presence bulky monophosphine ligand.

Language: Английский

Citations

2
Advances in Catalytic Asymmetric Hydrogen-Phosphine/Phosphorus Functionalization of Unsaturated Carbon-Carbon Bonds DOI

Ting-Jia Sun,

Guoyin Sun,

Wei Sun

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(12), P. 3647 - 3647

Published: Jan. 1, 2024

Language: Английский

Citations

0
Diastereoselective and Enantioselective Hydrophosphinylations of Conjugated Enynes, Allenes and Dienes via Synergistic Pd/Co Catalysis DOI

Minhao Tang,

Z. Yang,

Aijun Han

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 64(1)

Published: Sept. 10, 2024

Different from the reported work focusing on construction of single P- or C-stereocenter via hydrophosphinylation unsaturated carbon bonds, highly diastereo- and enantioselective reaction allenes, conjugated enynes 1,3-dienes is achieved a designed Pd/Co dual catalysis newly modified masked phosphinylating reagent. A series allyl motifs bearing both tertiary C- P-stereocenter are prepared in generally good yields, >20 : 1 dr, rr 99 % ee. The unprecedented 1,3-enynes established to generate skeletons containing nonadjacent chiral axis. first stereodivergent also developed achieve all four P-containing stereoisomers. present protocol features use only 3-minutes time 0.1 catalyst, with observation up 730 TON. set mechanistic studies reveal necessity roles two metal catalysts corroborate synergistic process.

Language: Английский

Citations

0
Enantioselective Hydrophosphination of Terminal Alkenyl Aza‐Heteroarenes DOI Creative Commons
Esther G. Sinnema, Tizian‐Frank Ramspoth, Reinder H. Bouma

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 136(7)

Published: Dec. 22, 2023

Abstract This paper presents a Mn(I)‐catalysed methodology for the enantioselective hydrophosphination of terminal alkenyl aza‐heteroarenes. The catalyst operates through H−P bond activation, enabling successful diverse range alkenyl‐heteroarenes with high enantioselectivity. presented protocol addresses inherently low reactivity and commonly encountered suboptimal enantioselectivities these challenging substrates. As an important application we show that this method facilitates synthesis non‐symmetric tridentate P,N,P‐containing ligand like structure in just two synthetic steps using single catalytic system.

Language: Английский

Citations

0