scholarly journals Nickel-catalyzed C-3 direct arylation of pyridinium ions for the synthesis of 1-azafluorenes

2016 ◽  
Vol 7 (8) ◽  
pp. 5581-5586 ◽  
Author(s):  
Jean-Nicolas Desrosiers ◽  
Xudong Wei ◽  
Osvaldo Gutierrez ◽  
Jolaine Savoie ◽  
Bo Qu ◽  
...  
Keyword(s):  
Precious Metal ◽  
Mechanistic Studies ◽  
Direct Arylation ◽  
Metal Catalyzed ◽  
Pyridinium Ions

The reactivity of pyridinium ions was utilized for the first non-precious-metal-catalyzed C-3 direct arylation and was demonstrated by mechanistic studies.

Aryl—Aryl Bond Formation by Transition-Metal-Catalyzed Direct Arylation

ChemInform ◽  
2007 ◽  
Vol 38 (22) ◽  
Author(s):  
Dino Alberico ◽  
Mark E. Scott ◽  
Mark Lautens
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Direct Arylation ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

scholarly journals Heterobiaryl synthesis by contractive C–C coupling via P(V) intermediates

Science ◽  
2018 ◽  
Vol 362 (6416) ◽  
pp. 799-804 ◽  
Author(s):  
Michael C. Hilton ◽  
Xuan Zhang ◽  
Benjamin T. Boyle ◽  
Juan V. Alegre-Requena ◽  
Robert S. Paton ◽  
...  
Keyword(s):  
Cross Coupling ◽  
The Other ◽  
Coupling Reactions ◽  
Mechanistic Studies ◽  
Alternative Approach ◽  
Metal Catalyzed ◽  
Polar Functional Groups ◽  
Pharmacological Function ◽  
Complex Drug ◽  
Acidic Alcohol

Heterobiaryls composed of pyridine and diazine rings are key components of pharmaceuticals and are often central to pharmacological function. We present an alternative approach to metal-catalyzed cross-coupling to make heterobiaryls using contractive phosphorus C–C couplings, also termed phosphorus ligand coupling reactions. The process starts by regioselective phosphorus substitution of the C–H bonds para to nitrogen in two successive heterocycles; ligand coupling is then triggered via acidic alcohol solutions to form the heterobiaryl bond. Mechanistic studies imply that ligand coupling is an asynchronous process involving migration of one heterocycle to the ipso position of the other around a central pentacoordinate P(V) atom. The strategy can be applied to complex drug-like molecules containing multiple reactive sites and polar functional groups, and also enables convergent coupling of drug fragments and late-stage heteroarylation of pharmaceuticals.

ChemInform Abstract: Discovery and Mechanistic Studies of a General Air-Promoted Metal-Catalyzed Aerobic N-Alkylation Reaction of Amides and Amines with Alcohols.

ChemInform ◽  
2011 ◽  
Vol 42 (48) ◽  
pp. no-no
Author(s):  
Chuanzhi Liu ◽  
Shiheng Liao ◽  
Qiang Li ◽  
Sunlin Feng ◽  
Xiaochun Yu ◽  
...  
Keyword(s):  
Alkylation Reaction ◽  
Mechanistic Studies ◽  
Metal Catalyzed

scholarly journals Weinreb Amides as Directing Groups for Transition Metal-Catalyzed C-H Functionalizations

Molecules ◽  
2019 ◽  
Vol 24 (5) ◽  
pp. 830 ◽  
Author(s):  
Jagadeesh Kalepu ◽  
Lukasz Pilarski
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
Metal Catalysts ◽  
Mechanistic Studies ◽  
Weinreb Amides ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Weinreb amides are a privileged, multi-functional group with well-established utility in classical synthesis. Recently, several studies have demonstrated the use of Weinreb amides as interesting substrates in transition metal-catalyzed C-H functionalization reactions. Herein, we review this part of the literature, including the metal catalysts, transformations explored so far and specific insights from mechanistic studies.

Discovery and Mechanistic Studies of a General Air-Promoted Metal-Catalyzed AerobicN-Alkylation Reaction of Amides and Amines with Alcohols

2011 ◽  
Vol 76 (14) ◽  
pp. 5759-5773 ◽  
Author(s):  
Chuanzhi Liu ◽  
Shiheng Liao ◽  
Qiang Li ◽  
Sunlin Feng ◽  
Qing Sun ◽  
...  
Keyword(s):  
Alkylation Reaction ◽  
Mechanistic Studies ◽  
Metal Catalyzed

Mechanistic studies and optimisation of a Pd-catalysed direct arylation reaction using phosphine-free systems

2015 ◽  
Vol 2 (5) ◽  
pp. 520-525 ◽  
Author(s):  
Junpei Kuwabara ◽  
Masaru Sakai ◽  
Qiao Zhang ◽  
Takaki Kanbara
Keyword(s):  
Initial Step ◽  
Mechanistic Study ◽  
Valuable Insight ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Direct Arylation

The mechanistic study of the initial step in direct arylation provides valuable insight for optimising reaction conditions.

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