(Semi)Hydrogenation of Enoates and Alkynes Effected by a Versatile, Particulate Copper Catalyst DOI
Samuel Redl, Christoph Topf

Published: Jan. 1, 2024

SUMMARYWe communicate a versatile and user-friendly Cu-based catalytic method that allows for the selective hydrogenation of enoates alkynes. The introduced protocol is free from any ex ante modifications used Cu(I) precursors by air-sensitive phosphines or elaborate N-heterocyclic carbene ligands. conjugate (selective) reduction C≡C bonds achieved through [Cu(CH3CN)4]+/tert-butoxide pair whereby we describe delicate influence base cation on chemoselectivity respective transformation. In case ester-to-alcohol reduction, combination simple CuI NaOtBu proved to be successful. Deuteration experiments are included address certain mechanistic aspects system. All requisite chemicals readily obtainable commercial channels catalyst assembly set up bench without need special lab-technical precautions.

Language: Английский

(Semi)hydrogenation of enoates and alkynes effected by a versatile, particulate copper catalyst DOI Creative Commons
Samuel Redl, Christoph Topf

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 12, P. 100089 - 100089

Published: Aug. 15, 2024

We communicate a versatile and user-friendly Cu-based catalytic method that allows for the selective hydrogenation of enoates alkynes. The introduced protocol is free from any ex ante modifications used Cu(I) precursors by air-sensitive phosphines or elaborate N-heterocyclic carbene ligands. conjugate (selective) reduction CC bonds achieved through [Cu(CH3CN)4]+/tert-butoxide pair whereby we describe delicate influence base cation on chemoselectivity respective transformation. In case ester-to-alcohol reduction, combination simple CuI NaOtBu proved to be successful. Deuteration experiments are included address certain mechanistic aspects system. All requisite chemicals readily obtainable commercial channels catalyst assembly set up bench without need special lab-technical precautions.Graphical abstract

Language: Английский

Citations

2
Nickel‐Catalyzed Stereospecific Deoxygenation of trans‐ Aromatic Epoxides to (Z)‐Alkenes: An Efficient Route to Access (Z)‐Cinnamic Acid Derivatives DOI
Sunisa Akkarasamiyo,

Saranya Chitsomkhuan,

Supawadee Buakaew

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(5)

Published: Feb. 16, 2024

Abstract A stereospecific deoxygenation of trans ‐epoxy cinnamic acid derivatives to access ( Z) ‐cinnamamides, ‐cinnamyl alcohol and amines using a catalytic system based on nickel triflate triphenylphosphine has been developed. The desired products were obtained in good excellent yield (up 92 % isolated yield) stereospecificity Z : E ratio up to>99 1). transformation broad functional group tolerance including amides, amines, alcohols esters. power the methodology was demonstrated key step total synthesis biologically active natural product, N‐cis‐ feruloyl tyramine from readily available ‐ferulic acid. reaction mechanism involving activation epoxide via coordination oxygen atom neighboring O‐ or N‐atoms catalyst formation Ph 3 P‐carbon bond is proposed. This method important for highly desirable functionalized ‐alkenes E)‐ alkenes.

Language: Английский

Citations

1
(Semi)Hydrogenation of Enoates and Alkynes Effected by a Versatile, Particulate Copper Catalyst DOI
Samuel Redl, Christoph Topf

Published: Jan. 1, 2024

SUMMARYWe communicate a versatile and user-friendly Cu-based catalytic method that allows for the selective hydrogenation of enoates alkynes. The introduced protocol is free from any ex ante modifications used Cu(I) precursors by air-sensitive phosphines or elaborate N-heterocyclic carbene ligands. conjugate (selective) reduction C≡C bonds achieved through [Cu(CH3CN)4]+/tert-butoxide pair whereby we describe delicate influence base cation on chemoselectivity respective transformation. In case ester-to-alcohol reduction, combination simple CuI NaOtBu proved to be successful. Deuteration experiments are included address certain mechanistic aspects system. All requisite chemicals readily obtainable commercial channels catalyst assembly set up bench without need special lab-technical precautions.

Language: Английский

Citations

0