Mechanism of Iron-Catalyzed Oxidative α-Amination of Ketones with Sulfonamides DOI Creative Commons

Gloria M. Parrales,

Nina C. Hollin,

Fubin Song

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 12462 - 12466

Опубликована: Авг. 16, 2024

We report the mechanism of iron-catalyzed oxidative α-amination ketones with sulfonamides. Using linear free energy relationships, competition experiments, and identification reaction intermediates, we have found that this proceeds through rate-limiting electron transfer to 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) from an iron enolate in process forming α-DDQ adduct. The adduct then serves as electrophile for substitution sulfonamide nucleophiles, accelerated by additional DDQ. This mechanistic study rules out formation α-carbocation intermediate purely radical hypotheses.

Язык: Английский

Electrosynthesis of iminophosphoranes and applications in nickel catalysis DOI Creative Commons
Velabo Mdluli, Dan Lehnherr, Yu‐hong Lam

и другие.

Chemical Science, Год журнала: 2024, Номер 15(16), С. 5980 - 5992

Опубликована: Янв. 1, 2024

N -Cyano iminophosphoranes are synthesized using electrochemistry and evaluated as ligands in various nickel-catalysed reactions. The electronic structural properties of these were studied both computationally experimentally.

Язык: Английский

Процитировано

7
Low-coordinate bis-phosphine and monophosphine Ni(0) complexes: synthesis and reactivity in C-S cross-coupling DOI Creative Commons

M. Trinidad Martín,

Carlos J. Carrasco,

Nazaret Santamaría

и другие.

Dalton Transactions, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Bis-phosphine and monophosphine Ni(0) complexes with bulky phosphine ligands are prepared tested in C–S cross-coupling reactions.

Язык: Английский

Процитировано

0
Advances in Accessing Rare Oxidation States of Nickel for Catalytic Innovation DOI

Aankhi Khamrai,

Sudipta Kumar Ghosh, Venkataraman Ganesh

и другие.

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Nickel catalysis has experienced a renaissance over the past two decades, driven by its ability to access diverse oxidation states (0 +4). This review consolidates advancements in nickel chemistry at various states.

Язык: Английский

Процитировано

0
Influence of the Counterion on the Activation of Nickel(σ-Aryl) Precatalysts DOI Creative Commons

Ivo H. Lindenmaier,

Anna S. Harzer,

Markus Ströbele

и другие.

Organometallics, Год журнала: 2025, Номер unknown

Опубликована: Фев. 2, 2025

Язык: Английский

Процитировано

0
The Use of Ni(cod)(dq) (COD: 1,5-Cyclooctadiene; DQ: Duroquinone) for the Dehalogenative Coupling Polycondensation to π-Conjugated Polyarylenes DOI

Naoki Noda,

Masahiro Umeda, Kentaro Okano

и другие.

Organic Process Research & Development, Год журнала: 2025, Номер unknown

Опубликована: Март 2, 2025

Язык: Английский

Процитировано

0
Industry’s Path to a Greener Future: A Perspective on Current Sustainable Practices and Areas of Opportunity DOI
Guillermo Lozano Onrubia, Durbis J. Castillo‐Pazos, Krystal Grieger

и другие.

ACS Sustainable Chemistry & Engineering, Год журнала: 2025, Номер unknown

Опубликована: Май 7, 2025

Язык: Английский

Процитировано

0
Ni0(cod)(dq) (COD: 1,5-cycloctadiene; DQ: duroquinone) complex as a catalyst precursor for oligothiophene and polythiophene synthesis DOI

Naoki Noda,

Seiha Yamaoka,

Ukyo Ogi

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(13), С. 2574 - 2579

Опубликована: Янв. 1, 2024

Ni(cod)(dq) effectively serves as a catalyst precursor for the preparation of well-defined oligothiophenes and polythiophenes.

Язык: Английский

Процитировано

2
Mechanism of Iron-Catalyzed Oxidative α-Amination of Ketones with Sulfonamides DOI Creative Commons

Gloria M. Parrales,

Nina C. Hollin,

Fubin Song

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 12462 - 12466

Опубликована: Авг. 16, 2024

We report the mechanism of iron-catalyzed oxidative α-amination ketones with sulfonamides. Using linear free energy relationships, competition experiments, and identification reaction intermediates, we have found that this proceeds through rate-limiting electron transfer to 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) from an iron enolate in process forming α-DDQ adduct. The adduct then serves as electrophile for substitution sulfonamide nucleophiles, accelerated by additional DDQ. This mechanistic study rules out formation α-carbocation intermediate purely radical hypotheses.

Язык: Английский

Процитировано

0