Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions

ACS Catalysis, Journal Year: 2020, Volume and Issue: 10(15), P. 8237 - 8246

Published: June 24, 2020

Nickel-catalyzed reductive cross-coupling reactions have emerged as powerful methods to join two electrophiles. These proven particularly useful for the coupling of sec-alkyl electrophiles form stereogenic centers; however, development enantioselective variants remains challenging. In this Perspective, we summarize progress that has been made toward Ni-catalyzed reactions.

Language: Английский

---

Mechanisms of Nickel-Catalyzed Cross-Coupling Reactions

Trends in Chemistry, Journal Year: 2019, Volume and Issue: 1(9), P. 830 - 844

Published: Sept. 13, 2019

Language: Английский

---

Saturated bioisosteres of benzene: where to go next?

Organic & Biomolecular Chemistry, Journal Year: 2019, Volume and Issue: 17(11), P. 2839 - 2849

Published: Jan. 1, 2019

Saturated bioisosteres for ortho- and meta-substituted benzenes remain a current challenge chemists.

Language: Английский

---

Single Electron Transfer-Induced Redox Processes Involving N-(Acyloxy)phthalimides

ACS Catalysis, Journal Year: 2021, Volume and Issue: 11(3), P. 1640 - 1683

Published: Jan. 20, 2021

The past decade has witnessed the emergence of N-(acyloxy)phthalimides (NHPI esters) and its derivatives at forefront synthetic methods facilitating construction diverse molecular frameworks from readily available carboxylic acid feedstock. NHPI esters are predisposed to undergo reductive fragmentation via a single electron transfer (SET) process under thermal, photochemical, or electrochemical conditions generate corresponding carbon- nitrogen-centered radicals that participate in multitude transformations forge carbon–carbon carbon–heteroatom bonds. chemistry involving received broad applicability not only well-designed cascade annulations but also medicinal natural product synthesis. This comprehensive Review, broadly categorized according nature bond formation, details progress made this field since initial discovery by providing representative examples with mechanistic details, an emphasis on challenges future directions.

Language: Английский

---

Reductive radical-polar crossover: traditional electrophiles in modern radical reactions

Chemical Science, Journal Year: 2019, Volume and Issue: 10(36), P. 8285 - 8291

Published: Jan. 1, 2019

The concept of reductive radical-polar crossover (RRPCO) reactions has recently emerged as a valuable and powerful tool to overcome limitations both radical traditional polar chemistry.

Language: Английский

---

Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids**

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(23), P. 9143 - 9148

Published: March 2, 2020

Abstract As a key element in the construction of complex organic scaffolds, formation C−C bonds remains challenge field synthetic chemistry. Recent advancements single‐electron chemistry have enabled new methods for various bonds. Disclosed herein is development novel reduction acyl azoliums ketones from carboxylic acids. Facile azolium situ followed by radical–radical coupling was made possible merging N‐heterocyclic carbene (NHC) and photoredox catalysis. The utility this protocol synthesis showcased late‐stage functionalization variety pharmaceutical compounds. Preliminary investigations using chiral NHCs demonstrate that enantioselectivity can be achieved, showcasing advantages over alternative methodologies.

Language: Английский

---

LiCl-Accelerated Multimetallic Cross-Coupling of Aryl Chlorides with Aryl Triflates

Journal of the American Chemical Society, Journal Year: 2019, Volume and Issue: 141(28), P. 10978 - 10983

Published: June 30, 2019

While the synthesis of biaryls has advanced rapidly in past decades, cross-Ullman couplings aryl chlorides, most abundant electrophiles, have remained elusive. Reported here is first general coupling chlorides with triflates. The selectivity challenge associated an inert electrophile a reactive one overcome using multimetallic strategy appropriate choice additive. Studies demonstrate that LiCl essential for effective cross-coupling by accelerating reduction Ni(II) to Ni(0) and counteracting autoinhibition at Zn(0) Zn(II) salts. modified conditions tolerate variety functional groups on either partner (42 examples), examples include three-step flurbiprofen.

Language: Английский

---

Nickel-catalyzed formation of quaternary carbon centers using tertiary alkyl electrophiles

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(6), P. 4162 - 4184

Published: Jan. 1, 2021

This review provides a comprehensive summary of recent advances in nickel-catalyzed reactions employing tertiary alkyl electrophiles for the construction quaternary carbon centers.

Language: Английский

---

Dialkylation of 1,3-Dienes by Dual Photoredox and Chromium Catalysis

ACS Catalysis, Journal Year: 2019, Volume and Issue: 10(2), P. 1621 - 1627

Published: Dec. 18, 2019

The direct conversion of feedstock chemicals into value-added products is broad interest in chemical research. Herein, we present a regioselective and diastereoselective three-component dialkylation 1,3-dienes with Hantzsch esters aldehydes for the synthesis homoallylic alcohols. reaction enabled by dual photoredox chromium catalysis can also be performed enantioselectively employing chromium-bisoxazoline complexes.

Language: Английский

---

Direct decarboxylative Giese reactions

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(4), P. 1415 - 1453

Published: Jan. 1, 2022

This review summarizes recent progress on using carboxylic acids directly as convenient precursors for the 1,4-radical conjugate addition (Giese) reaction.

Language: Английский

---