Springboard Role for Iridium Photocatalyst: Theoretical Insight of C(sp3)‒N Cross‐Coupling by Photoredox‐Mediated Iridium/Copper Dual Catalysis versus Single‐Copper Catalysis

ChemCatChem ◽  
2022 ◽  
Author(s):  
Run-Han Li ◽  
Shuang Wang ◽  
Zhi-Wen Zhao ◽  
Yun Geng ◽  
Xin-Long Wang ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Copper Catalysis ◽  
Dual Catalysis ◽  
Theoretical Insight

Concise Synthesis of GB22 by Endo-Selective Siloxycyclopropane Arylation

2019 ◽  
Author(s):  
Hannah E. Burdge ◽  
Takuya Oguma ◽  
Takahiro Kawajiri ◽  
Ryan Shenvi
Keyword(s):  
Intramolecular Cyclization ◽  
Cross Coupling ◽  
Building Blocks ◽  
Ring Expansion ◽  
Dual Catalysis ◽  
Acid Labile

<div><div><div><p>The first synthesis of GB22 was accomplished by a con- cise, modular route. Two building blocks converged in a novel sp3-sp2 attached-ring coupling that used Ir/Ni dual-catalysis to reverse the regioselectivity of siloxycy- clopropane arylation. This cross-coupling proved general to access β-substituted tetralones via ring-expansion of indanone-derived siloxycyclopropanes. The congested, bridging rings of the GB alkaloids were completed using an aluminum-HFIP complex that effected intramolecular cyclization of an acid-labile substrate.</p></div></div></div>

Concise Synthesis of GB22 by Endo-Selective Siloxycyclopropane Arylation

2019 ◽  
Author(s):  
Hannah E. Burdge ◽  
Takuya Oguma ◽  
Takahiro Kawajiri ◽  
Ryan Shenvi
Keyword(s):  
Intramolecular Cyclization ◽  
Cross Coupling ◽  
Building Blocks ◽  
Ring Expansion ◽  
Dual Catalysis ◽  
Acid Labile

<div><div><div><p>The first synthesis of GB22 was accomplished by a con- cise, modular route. Two building blocks converged in a novel sp3-sp2 attached-ring coupling that used Ir/Ni dual-catalysis to reverse the regioselectivity of siloxycy- clopropane arylation. This cross-coupling proved general to access β-substituted tetralones via ring-expansion of indanone-derived siloxycyclopropanes. The congested, bridging rings of the GB alkaloids were completed using an aluminum-HFIP complex that effected intramolecular cyclization of an acid-labile substrate.</p></div></div></div>

scholarly journals Reductive Cross-Coupling of Conjugated Arylalkenes and Aryl Bromides with Hydrosilanes by Cooperative Palladium/Copper Catalysis

2016 ◽  
Vol 55 (21) ◽  
pp. 6275-6279 ◽  
Author(s):  
Kazuhiko Semba ◽  
Kenta Ariyama ◽  
Hong Zheng ◽  
Ryohei Kameyama ◽  
Shigeyoshi Sakaki ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Copper Catalysis ◽  
Aryl Bromides

ChemInform Abstract: Reductive Cross-Coupling of Conjugated Arylalkenes and Aryl Bromides with Hydrosilanes by Cooperative Palladium/Copper Catalysis.

ChemInform ◽  
2016 ◽  
Vol 47 (39) ◽  
Author(s):  
Kazuhiko Semba ◽  
Kenta Ariyama ◽  
Hong Zheng ◽  
Ryohei Kameyama ◽  
Shigeyoshi Sakaki ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Copper Catalysis ◽  
Aryl Bromides

scholarly journals Photoredox Ni-catalyzed peptide C(sp2)–O cross-coupling: from intermolecular reactions to side chain-to-tail macrocyclization

2019 ◽  
Vol 10 (19) ◽  
pp. 5073-5078 ◽  
Author(s):  
Hyelee Lee ◽  
Nicolas C. Boyer ◽  
Qiaolin Deng ◽  
Hai-Young Kim ◽  
Tomi K. Sawyer ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Side Chain ◽  
Coupling Reactions ◽  
Intermolecular Reactions ◽  
Dual Catalysis

Ni/photoredox (4DPAIPN) dual catalysis enabled challenging peptide C(sp2)–O coupling reactions.

Rapid threefold cross-couplings with sterically bulky triarylbismuths under Pd–Cu dual catalysis

RSC Advances ◽  
2016 ◽  
Vol 6 (2) ◽  
pp. 1012-1017 ◽  
Author(s):  
Maddali L. N. Rao ◽  
Ritesh J. Dhanorkar
Keyword(s):  
Cross Coupling ◽  
Dual Catalysis

The threefold cross-coupling reactivity of sterically highly demanding bulky triarylbismuths was addressed with task specific Pd–Cu dual catalytic conditions.

scholarly journals Photoredox Cross-Coupling: Ir/Ni Dual Catalysis for the Synthesis of Benzylic Ethers

2015 ◽  
Vol 17 (13) ◽  
pp. 3294-3297 ◽  
Author(s):  
Idris Karakaya ◽  
David N. Primer ◽  
Gary A. Molander
Keyword(s):  
Cross Coupling ◽  
Dual Catalysis

scholarly journals Cross-Coupling of Sodium Sulfinates with Aryl, Heteroaryl, and Vinyl Halides by Nickel/Photoredox Dual Catalysis

2018 ◽  
Vol 130 (5) ◽  
pp. 1385-1389 ◽  
Author(s):  
Huifeng Yue ◽  
Chen Zhu ◽  
Magnus Rueping
Keyword(s):  
Cross Coupling ◽  
Vinyl Halides ◽  
Dual Catalysis

scholarly journals Cross-Coupling of Alkyl Redox-Active Esters with Benzophenone Imines: Tandem Photoredox and Copper Catalysis

2018 ◽  
Vol 130 (30) ◽  
pp. 9645-9648 ◽  
Author(s):  
Runze Mao ◽  
Jonathan Balon ◽  
Xile Hu
Keyword(s):  
Cross Coupling ◽  
Copper Catalysis ◽  
Active Esters ◽  
Redox Active

scholarly journals Primary alkyl bis-catecholato silicates in dual photoredox/nickel catalysis: aryl- and heteroaryl-alkyl cross coupling reactions

2016 ◽  
Vol 3 (4) ◽  
pp. 462-465 ◽  
Author(s):  
Christophe Lévêque ◽  
Ludwig Chenneberg ◽  
Vincent Corcé ◽  
Jean-Philippe Goddard ◽  
Cyril Ollivier ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Nickel Catalysis ◽  
Cross Coupling Reactions ◽  
Dual Catalysis

Primary alkyl bis-catecholato silicates have been successfully engaged with aryl and heteroaryl bromide substrates in photoredox/nickel dual catalysis to provide cross coupling products.

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