Oxygen‐Linked Cyclopentadienyl Rhodium(III) Complexes‐Catalyzed Asymmetric C−H Arylation of Benzo[h]quinolines with 1‐Diazonaphthoquinones DOI
Chongqing Pan,

Si‐Yong Yin,

Shao‐Bo Wang

и другие.

Angewandte Chemie International Edition, Год журнала: 2021, Номер 60(28), С. 15510 - 15516

Опубликована: Апрель 16, 2021

Abstract Chiral cyclopentadienyl rhodium (CpRh) complex‐catalyzed asymmetric C−H functionalization reactions have witnessed a significant progress in organic synthesis. In sharp contrast, the reported chiral Cp ligands are limited to C‐linked and often synthetically challenging. To address these issues, we developed novel class of tunable bearing oxygen linkers, which were efficient catalysts for arylation benzo[ h ]quinolines with 1‐diazonaphthoquinones, affording axially heterobiaryls excellent yields enantioselectivity (up 99 % yield, 98.5:1.5 er). Mechanistic studies suggest that reaction is likely proceed by electrophilic activation, followed coupling cyclometalated rhodium(III) complex 1‐diazonaphthoquinones.

Язык: Английский

Cobalt(III)‐Catalyzed Enantioselective Intermolecular Carboamination by C−H Functionalization DOI

Kristers Ozols,

Shunsuke Onodera,

Łukasz Woźniak

и другие.

Angewandte Chemie International Edition, Год журнала: 2020, Номер 60(2), С. 655 - 659

Опубликована: Сен. 28, 2020

Abstract High‐valent cyclopentadienyl cobalt catalysis is a versatile tool for sustainable C−H bond functionalizations. To harness the full potential of this strategy, control stereoselectivity these processes necessary. Herein, we report highly enantioselective intermolecular carboaminations alkenes through activation N ‐phenoxyamides catalyzed by Co III ‐complexes equipped with chiral (Cp x ) ligands. The method converts widely available acrylates as well bicyclic olefins into attractive enantioenriched isotyrosine derivatives elaborated amino‐substituted scaffolds under very mild conditions. outlined reactivity unique to Cp complexes and complementary 4d‐ 5d‐ precious‐metal catalysts.

Язык: Английский

Процитировано

112
Access to P‐ and Axially Chiral Biaryl Phosphine Oxides by Enantioselective CpxIrIII‐Catalyzed C−H Arylations DOI

Yun‐Suk Jang,

Łukasz Woźniak, Julia Pedroni

и другие.

Angewandte Chemie, Год журнала: 2018, Номер 130(39), С. 13083 - 13087

Опубликована: Июль 25, 2018

Abstract An enantioselective C−H arylation of phosphine oxides with o ‐quinone diazides catalyzed by an iridium(III) complex bearing atropchiral cyclopentadienyl (Cp x ) ligand and phthaloyl tert ‐leucine as co‐catalyst is reported. The method allows access to a) P ‐chiral biaryl oxides, b) atropo‐enantioselective construction sterically demanding backbones, also c) selective assembly axial compounds in excellent yields diastereo‐ enantioselectivities. Enantiospecific reductions provide monodentate chiral phosphorus(III) having structures backbones proven importance ligands asymmetric catalysis.

Язык: Английский

Процитировано

108
Enantioselektive C‐H‐Aktivierung mit natürlich vorkommenden 3d‐Übergangsmetallen DOI
Joachim Loup, Uttam Dhawa, Fabio Pesciaioli

и другие.

Angewandte Chemie, Год журнала: 2019, Номер 131(37), С. 12934 - 12949

Опубликована: Май 11, 2019

Abstract Molekulare Synthese basiert größtenteils auf zeit‐ und arbeitsintensiven Präfunktionalisierungsstrategien. Demgegenüber bietet die C‐H‐Aktivierung ein leistungsstarkes Hilfsmittel, das ohne lange Synthesen präfunktionalisierter Substrate auskommt großes Potenzial für z. B. Wirkstoffentwicklung, pharmazeutische Industrie, Materialwissenschaften von Pflanzenschutzmitteln hat. Die enantioselektive Funktionalisierung omnipräsenter C‐H‐Bindungen hat sich zu einer etablierten Methode stufen‐ atomökonomische komplexer chiraler Moleküle entwickelt. Allerdings ist dieses rasant wachsende Feld durch Verwendung edler Übergangsmetalle geprägt, mit besonderer Präsenz toxischer Palladium‐, Iridium‐ Rhodiumkatalysatoren. Trotz bedeutender Errungenschaften befindet asymmetrische unter kostengünstiger nachhaltiger 3d‐Metalle noch im Anfangsstadium. In diesem Kurzaufsatz diskutieren wir neuen, herausragenden Fortschritte bei enantioselektiven Transformationen über metallorganische C‐H‐Aktivierungen 3d‐Basismetalle bis April 2019.

Процитировано

107
Palladium-catalyzed asymmetric hydrophosphorylation of alkynes: facile access to P-stereogenic phosphinates DOI Creative Commons
Zhiping Yang,

Xiaodong Gu,

Li‐Biao Han

и другие.

Chemical Science, Год журнала: 2020, Номер 11(28), С. 7451 - 7455

Опубликована: Янв. 1, 2020

A catalytic enantioselective synthesis of P-stereogenic alkenylphosphinates is developed through asymmetric hydrophosphorylation. This process demonstrated on racemic phosphinates and leads to diverse directly.

Язык: Английский

Процитировано

107
Oxygen‐Linked Cyclopentadienyl Rhodium(III) Complexes‐Catalyzed Asymmetric C−H Arylation of Benzo[h]quinolines with 1‐Diazonaphthoquinones DOI
Chongqing Pan,

Si‐Yong Yin,

Shao‐Bo Wang

и другие.

Angewandte Chemie International Edition, Год журнала: 2021, Номер 60(28), С. 15510 - 15516

Опубликована: Апрель 16, 2021

Abstract Chiral cyclopentadienyl rhodium (CpRh) complex‐catalyzed asymmetric C−H functionalization reactions have witnessed a significant progress in organic synthesis. In sharp contrast, the reported chiral Cp ligands are limited to C‐linked and often synthetically challenging. To address these issues, we developed novel class of tunable bearing oxygen linkers, which were efficient catalysts for arylation benzo[ h ]quinolines with 1‐diazonaphthoquinones, affording axially heterobiaryls excellent yields enantioselectivity (up 99 % yield, 98.5:1.5 er). Mechanistic studies suggest that reaction is likely proceed by electrophilic activation, followed coupling cyclometalated rhodium(III) complex 1‐diazonaphthoquinones.

Язык: Английский

Процитировано

104