Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions

Poremba, Kelsey E.; Dibrell, Sara E.; Reisman, Sarah E.

doi:10.1021/acscatal.0c01842

Cited by 458 publications

(187 citation statements)

References 114 publications

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“…Merging photoredox and Cu catalysis offers new avenues for stereoselective transformations by providing a dual catalytic manifold in which efficient radical generation and stereocontrolled product formation generally occur in two separate cycles [3d, 30] …”

Section: Enantioselective Transformationsmentioning

confidence: 99%

Stereoinduction in Metallaphotoredox Catalysis

2020

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Gary Molander completed his undergraduate studies in chemistry at Iowa State University under the tutelageo fP rofessor Richard C. Larock. He earned his PhD at Purdue University with Professor HerbertC. Brown and undertook postdoctoral training with Professor Barry M. Trost at the University of Wisconsin, Madison. He began his academic career at the University of Colorado, Boulder,m oving to the University of Pennsylvaniai n1 999, where he is currently the Hirschmann-Makineni Professor of Chemistry. Scheme 2. Enantioselective photoredox/Ni dual-catalyzed cross-coupling of A) a-trifluoromethyltrifluoroborates and B) a-alkoxymethyltrifluoroborates. Scheme 3. Enantioselective photoredox/Ni dual-catalyzed desymmetrization of A) cyclic meso anhydrides and B) diols. Angewandte Chemie Minireviews Scheme 4. Enantioselective photoredox/Ni dual-catalyzed decarboxylative arylations. Scheme 5. Enantioselective photoredox/Ni dual-catalyzed C(sp 3)-H arylation. Angewandte Chemie Minireviews Scheme 9. Enantioselective photoredox/Ni dual-catalyzed 1,2-carbodifunctionalization of carbamoyl chloride-tethered alkenes. Scheme 10. Mechanism involving photoexcitation of aCu I complex and reductive elimination from Cu III. Scheme 11. Enantioselective C-N cross-couplingoftertiary a-chloroamides with carbazoles and indoles. Scheme 12. Interposing aGiese-type addition prior to formation of the Cu III intermediate enables A) cyanation/fluoroalkylation and B) alkylation/alkynylation or arylation/alkynylationo falkenes. Angewandte Chemie Minireviews Scheme 23. Diastereoselective photoredox/Ni dual-catalyzed 1,2-carbosulfonylationo falkynes.

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Section: Enantioselective Transformationsmentioning

confidence: 99%

Stereoinduction in Metallaphotoredox Catalysis

2020

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“…Control experiments confirmed that all components (Ni, ligand, current, additive) were essential for the reaction outcome. Although not specifically discussed in the paper, the cross-coupling has been considered to follow a sequential reduction mechanism [118,119] taking into account results that proved inconsistent with a radical chain mechanism for the non-electrochemically-driven variant of the reaction [120]. In the sequential reduction pathway, a Ni 0 complex would be generated from electroreduction of the Ni II precursor, and the C(sp 2 ) coupling partner (the alkenyl bromide) would undergo oxidative addition with this Ni 0 species.…”

Section: Cross-electrophile Couplingsmentioning

confidence: 99%

Recent Advances in Asymmetric Catalytic Electrosynthesis

Margarita

Lundberg

2020

Catalysts

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The renewed interest in electrosynthesis demonstrated by organic chemists in the last years has allowed for rapid development of new methodologies. In this review, advances in enantioselective electrosynthesis that rely on catalytic amounts of organic or metal-based chiral mediators are highlighted with focus on the most recent developments up to July 2020. Examples of C-H functionalization, alkene functionalization, carboxylation and cross-electrophile couplings are discussed, along with their related mechanistic aspects.

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“…Die Kombination von Photoredox‐ und Cu‐Katalyse bietet neue Möglichkeiten für stereoselektive Transformationen, wobei die effiziente Generierung von Radikalen sowie die stereokontrollierte Produktbildung generell in zwei separaten Katalysezyklen erfolgen [3d, 30] …”

Section: Enantioselektive Transformationenunclassified

“…2014 hat unsere Gruppe die erste duale Photoredox/Ni-Katalyse zur Konstruktion von C(sp 2 )-C(sp 3 )-Bindungen unter milden Reaktionsbedingungen beschrieben, welche mit zahlreichen funktionellen Gruppen kompatibel ist (Schema 1A). [1a] In diesem Bericht wurde gezeigt, dass Benzyltrifluoroborate (E 1/2 =+1.10 Vg egen SCE) oxidativ fragmentieren und dabei Radikale bilden, welche in Ni-katalysierten Kreuzkupplungen eingesetzt werden kçnnen.…”

Section: Ni-katalysierte Enantioselektive Transformationenunclassified

“…[2] In den vergangenen Jahren hat der Einsatz chiraler Liganden in photochemischen Transformationen neue Zugänge zu asymmetrischen Bindungsbildungen ermçglicht. [3] Obgleich beachtliche Fortschritte auf diesem Gebiet erzielt wurden, sind solche stereoselektiven Reaktionen aus Synthesesicht noch nicht ausreichend entwickelt. Des Weiteren gibt es noch Lücken im mechanistischen Verständnis dieser Prozesse,b esonders bezüglich des Ursprungs der Stereoinduktion.…”

Section: Introductionunclassified

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Stereoinduktion in der Metallaphotoredoxkatalyse

2020

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Gary Molander schloss sein Studium der Chemie an der Iowa State University unter der Anleitung von Professor Richard C. Larock ab. Auf seine Promotion an der Purdue University in der Gruppe von Professor Herbert C. Brown folgte ein Forschungsaufenthalt bei ProfessorB arry M. Trost an der University of Wisconsin, Madison. Er begann seine akademische Laufbahn an der University of Colorado, Boulderu nd wechselte 1999 an die University of Pennsylvania, wo er aktuell als Hirschmann-Makineni-Professor fürC hemie tätig ist. Schema 1. Enantioselektive Kreuzkupplung mit Benzyltrifluoroboraten durch duale Photoredox/Ni-Katalyse. Schema 2. Enantioselektive Kreuzkupplung mit A) a-Trifluormethyltrifluoroboratenu nd B) a-Alkoxymethyltrifluoroboratendurch duale Photoredox/Ni-Katalyse.

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Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions

Cited by 458 publications

References 114 publications

Stereoinduction in Metallaphotoredox Catalysis

Stereoinduction in Metallaphotoredox Catalysis

Recent Advances in Asymmetric Catalytic Electrosynthesis

Stereoinduktion in der Metallaphotoredoxkatalyse

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