Iridium-Catalyzed Chemoselective and Enantioselective Hydrogenation of (1-Chloro-1-Alkenyl) Boronic Esters

2011 ◽  
Vol 124 (4) ◽  
pp. 1038-1042 ◽  
Author(s):  
Ivana Gazić Smilović ◽  
Eva Casas-Arcé ◽  
Stephen J. Roseblade ◽  
Ulrike Nettekoven ◽  
Antonio Zanotti-Gerosa ◽  
...  
Keyword(s):  
Enantioselective Hydrogenation ◽  
Boronic Esters

Iridium-Catalyzed Chemoselective and Enantioselective Hydrogenation of (1-Chloro-1-Alkenyl) Boronic Esters

2011 ◽  
Vol 51 (4) ◽  
pp. 1014-1018 ◽  
Author(s):  
Ivana Gazić Smilović ◽  
Eva Casas-Arcé ◽  
Stephen J. Roseblade ◽  
Ulrike Nettekoven ◽  
Antonio Zanotti-Gerosa ◽  
...  
Keyword(s):  
Enantioselective Hydrogenation ◽  
Boronic Esters

ChemInform Abstract: Iridium-Catalyzed Chemoselective and Enantioselective Hydrogenation of (1-Chloro-1-alkenyl) Boronic Esters.

ChemInform ◽  
2012 ◽  
Vol 43 (24) ◽  
pp. no-no
Author(s):  
Ivana Gazic Smilovi ◽  
Eva Casas-Arce ◽  
Stephen J. Roseblade ◽  
Ulrike Nettekoven ◽  
Antonio Zanotti-Gerosa ◽  
...  
Keyword(s):  
Enantioselective Hydrogenation ◽  
Boronic Esters

An Iron-Based Catalyst Enables The Enantioconvergent Synthesis of Chiral 1,1-Diarylalkanes Through a Suzuki-Miyaura Cross-Coupling Reaction

2020 ◽  
Author(s):  
Chet Tyrol ◽  
Nang Yone ◽  
Connor Gallin ◽  
Jeffery Byers
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Radical Intermediates ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Boronic Esters ◽  
Carbon Centered Radical ◽  
Iron Based ◽  
High Yields

By using an iron-based catalyst, access to enantioenriched 1,1-diarylakanes was enabled through an enantioselective Suzuki-Miyaura crosscoupling reaction. The combination of a chiral cyanobis(oxazoline) ligand framework and 1,3,5-trimethoxybenzene additive were essential to afford high yields and enantioselectivities in cross-coupling reactions between unactivated aryl boronic esters and a variety of benzylic chlorides, including challenging ortho-substituted benzylic chloride substrates. Mechanistic investigations implicate a stereoconvergent pathway involving carbon-centered radical intermediates.

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