Mechanistic Studies of a Pd-Catalyzed Direct Arylation En Route to Beclabuvir: Dual Role of a Tetramethylammonium Cation and an Unusual Turnover-Limiting Step

ACS Catalysis ◽  
2021 ◽  
pp. 2460-2472
Author(s):  
Chao Hang ◽  
Antonio Ramirez ◽  
Collin Chan ◽  
Yi Hsiao ◽  
Albert J. DelMonte ◽  
...  
Keyword(s):  
Dual Role ◽  
Mechanistic Studies ◽  
Direct Arylation ◽  
Limiting Step

Dual role of carboxylic acid additive: mechanistic studies and implication for the asymmetric C–H amidation

Tetrahedron ◽  
2015 ◽  
Vol 71 (26-27) ◽  
pp. 4504-4511 ◽  
Author(s):  
Donghyeon Gwon ◽  
Sehoon Park ◽  
Sukbok Chang
Keyword(s):  
Carboxylic Acid ◽  
Dual Role ◽  
Mechanistic Studies

Dual role of B7 costimulation in obesity-related non-alcoholic steatohepatitis (NASH) and metabolic dysregulation

2014 ◽  
Vol 122 (03) ◽  
Author(s):  
A Chatzigeorgiou ◽  
R Garcia-Martin ◽  
KJ Chung ◽  
I Alexaki ◽  
A Klotzsche-von Ameln ◽  
...  
Keyword(s):  
Dual Role ◽  
Alcoholic Steatohepatitis ◽  
Metabolic Dysregulation

A dual role of the N-terminal FQQI motif in GLUT4 trafficking

2008 ◽  
Vol 3 (S 1) ◽  
Author(s):  
U Bernhardt ◽  
HG Joost ◽  
H Al-Hasani
Keyword(s):  
Dual Role

Dual Role of RKIP in NF-kB Signaling Pathways

2011 ◽  
Vol 2 (1) ◽  
pp. 21-34
Author(s):  
Huihui Tang ◽  
Sungdae Park ◽  
Kam C. Yeung
Keyword(s):  
Signaling Pathways ◽  
Dual Role

Synthetic and Mechanistic Studies of a Versatile Heteroaryl Thioether Directing Group for Pd(II) Catalysis

2019 ◽  
Author(s):  
Andrew Romine ◽  
Kin Yang ◽  
Malkanthi Karunananda ◽  
Jason Chen ◽  
Keary Engle
Keyword(s):  
Mechanistic Studies ◽  
Salvianolic Acid ◽  
Wide Range ◽  
Computational Data ◽  
Synthetic Utility ◽  
Directing Group ◽  
High Yields ◽  
Julia Olefination ◽  
Reaction Progress Kinetic Analysis

A weakly coordinating monodentate heteroaryl thioether directing group has been developed for use in Pd(II) catalysis to orchestrate key elementary steps in the catalytic cycle that require conformational flexibility in a manner that is difficult to accomplish with traditional strongly coordinating directing groups. This benzothiazole thioether, (BT)S, directing group can be used to promote oxidative Heck reactivity of internal alkenes providing a wide range of products in moderate to high yields. To demonstrate the broad applicability of this directing group, arene C–H olefination was also successfully developed. Reaction progress kinetic analysis provides insights into the role of the directing group in each reaction, which is supplemented with computational data for the oxidative Heck reaction. Furthermore, this (BT)S directing group can be transformed into a number of synthetically useful functional groups, including a sulfone for Julia olefination, allowing it to serve as a “masked olefin” directing group in synthetic planning. In order to demonstrate this synthetic utility, natural products (+)-salvianolic acid A and salvianolic acid F are formally synthesized using the (BT)S directed C–H olefination as the key step.

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