scholarly journals Tertiary amine synthesis via reductive coupling of amides with Grignard reagents

2017 ◽  
Vol 8 (11) ◽  
pp. 7492-7497 ◽  
Author(s):  
Lan-Gui Xie ◽  
Darren J. Dixon
Keyword(s):  
Tertiary Amine ◽  
Coupling Reaction ◽  
Grignard Reagents ◽  
Reductive Coupling ◽  
Tertiary Amides

A new iridium catalyzed reductive coupling reaction of Grignard reagents and tertiary amides affording functionalised tertiary amine products is described.

Iridium‐Catalyzed Reductive Coupling of Grignard Reagents and Tertiary Amides

2020 ◽  
pp. 1-17
Author(s):  
Pablo Gabriel ◽  
Lan‐Gui Xie ◽  
Darren J. Dixon* ◽  
Karli R. Holman ◽  
Sarah E. Reisman
Keyword(s):  
Grignard Reagents ◽  
Reductive Coupling ◽  
Tertiary Amides

scholarly journals Phosphite-Mediated Reductive Cross-Coupling of Isatins and Nitro­styrenes

Synthesis ◽  
2017 ◽  
Vol 49 (12) ◽  
pp. 2663-2676 ◽  
Author(s):  
Somayeh Motevalli ◽  
Jeffrey Johnson
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Reductive Coupling ◽  
Title Reaction ◽  
Dimethyl Phosphite ◽  
Mild Conditions ◽  
Michael Type Addition

A new reductive coupling reaction between N-alkylisatins, dimethyl phosphite, and nitrostyrenes has been developed. The reaction relies on Pudovik addition, subsequent phosphonate–phosphate rearrangement, and Michael-type addition of a transient carbanion on the indolinone with β-nitrostyrenes. This protocol introduces a convenient and versatile method for the construction of polyfunctionalized tertiary phosphates under mild conditions. Chiral general bases catalyze the title reaction with promising levels of enantioselectivity.

The role of oligomers in the synthesis of polysilanes by the Wurtz reductive coupling reaction

2003 ◽  
Vol 685 (1-2) ◽  
pp. 60-64 ◽  
Author(s):  
Daniel Bratton ◽  
Simon J. Holder ◽  
Richard G. Jones ◽  
William K.C. Wong
Keyword(s):  
Coupling Reaction ◽  
Reductive Coupling

One-pot synthesis of amides from carboxylic acids activated using thionyl chloride

RSC Advances ◽  
2016 ◽  
Vol 6 (41) ◽  
pp. 34468-34475 ◽  
Author(s):  
A. Leggio ◽  
E. L. Belsito ◽  
G. De Luca ◽  
M. L. Di Gioia ◽  
V. Leotta ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Tertiary Amine ◽  
Thionyl Chloride ◽  
One Pot ◽  
One Pot Synthesis ◽  
Tertiary Amides

We report on a one-pot synthesis of secondary and tertiary amides from carboxylic acids and amines in the presence of a tertiary amine by using thionyl chloride.

scholarly journals General α-Amino 1,3,4-Oxadiazole Synthesis via Late-Stage Reductive Functionalization of Tertiary Amides and Lactams

2021 ◽  
Author(s):  
Daniel Matheau-Raven ◽  
Darren J. Dixon
Keyword(s):  
Carboxylic Acid ◽  
Late Stage ◽  
Coupling Reaction ◽  
Reductive Activation ◽  
Mild Conditions ◽  
Drug Molecules ◽  
Drug Conjugates ◽  
Iminium Ion ◽  
Tertiary Amides ◽  
Coupling Partner

An iridium-catalyzed reductive three-component coupling reaction for the synthesis of medicinally relevant α-amino 1,3,4-oxadiazoles from abundant tertiary amides or lactams, carboxylic acids, and (N-isocyanimino) triphenylphosphorane, is described. Proceeding under mild conditions using (<1 mol%) Vaska’s complex (IrCl(CO)(PPh<sub>3</sub>)<sub>2</sub>) and tetramethyldisiloxane to access the key reactive iminium ion intermediates, a broad range of structurally complex α-amino 1,3,4-oxadiazole architectures were efficiently accessed from diverse carboxylic acid feedstock coupling partners. Extension to α-amino heterodiazole synthesis was readily achieved by exchanging the carboxylic acid coupling partner for C-, S-, or N-centered Brønsted acids, and provided rapid and modular access to these desirable, yet difficult-to-access, heterocycles. Furthermore, the high chemoselectivity of the catalytic reductive activation step allowed the late-stage functionalization of 10 drug molecules, including the synthesis of novel heterodiazole-fused drug-drug conjugates.<br>

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