scholarly journals Acyl azide generation and amide bond formation in continuous-flow for the synthesis of peptides

2020 ◽  
Vol 5 (4) ◽  
pp. 645-650 ◽  
Author(s):  
Alejandro Mata ◽  
Ulrich Weigl ◽  
Oliver Flögel ◽  
Pius Baur ◽  
Christopher A. Hone ◽  
...  
Keyword(s):  
Continuous Flow ◽  
Nitrous Acid ◽  
Flow System ◽  
Bond Formation ◽  
Amide Bond ◽  
Peptide Coupling ◽  
Amide Bond Formation ◽  
Acyl Azides ◽  
Acyl Azide

Acyl azides were safely generated by using nitrous acid in water and reacted in situ within a flow system. The acyl azide was efficiently extracted into the organic phase containing an amine nucleophile for a highly enantioselective peptide coupling.

scholarly journals Visible Light-Promoted Amide Bond Formation via One-Pot Nitrone in Situ Formation/Rearrangement Cascade

CCS Chemistry ◽  
2020 ◽  
pp. 2764-2771
Author(s):  
Bao-Gui Cai ◽  
Shuai-Shuai Luo ◽  
Lin Li ◽  
Lei Li ◽  
Jun Xuan ◽  
...  
Keyword(s):  
Visible Light ◽  
Bond Formation ◽  
Amide Bond ◽  
One Pot ◽  
Amide Bond Formation ◽  
In Situ Formation

scholarly journals Poly(methylhydrosiloxane) as a green reducing agent in organophosphorus-catalysed amide bond formation

2017 ◽  
Vol 15 (30) ◽  
pp. 6426-6432 ◽  
Author(s):  
Daan F. J. Hamstra ◽  
Danny C. Lenstra ◽  
Tjeu J. Koenders ◽  
Floris P. J. T. Rutjes ◽  
Jasmin Mecinović
Keyword(s):  
Carboxylic Acids ◽  
Phosphine Oxide ◽  
Bond Formation ◽  
Reducing Agent ◽  
Amide Bond ◽  
Amide Bond Formation ◽  
Amidation Reaction

In situ reduction of phosphine oxide by poly(methylhydrosiloxane) leads to efficient amidation reaction between carboxylic acids and amines.

Amide bond formation and peptide coupling

Tetrahedron ◽  
2005 ◽  
Vol 61 (46) ◽  
pp. 10827-10852 ◽  
Author(s):  
Christian A.G.N. Montalbetti ◽  
Virginie Falque
Keyword(s):  
Bond Formation ◽  
Amide Bond ◽  
Peptide Coupling ◽  
Amide Bond Formation

Amide Bond Formation and Peptide Coupling

ChemInform ◽  
2006 ◽  
Vol 37 (6) ◽  
Author(s):  
Christian A. G. N. Montalbetti ◽  
Virginie Falque
Keyword(s):  
Bond Formation ◽  
Amide Bond ◽  
Peptide Coupling ◽  
Amide Bond Formation

scholarly journals A protocol for amide bond formation with electron deficient amines and sterically hindered substrates

2016 ◽  
Vol 14 (2) ◽  
pp. 430-433 ◽  
Author(s):  
Maria E. Due-Hansen ◽  
Sunil K. Pandey ◽  
Elisabeth Christiansen ◽  
Rikke Andersen ◽  
Steffen V. F. Hansen ◽  
...  
Keyword(s):  
Elevated Temperature ◽  
Bond Formation ◽  
Amide Bond ◽  
Standard Methods ◽  
Amide Bond Formation ◽  
Amide Coupling ◽  
Sterically Hindered

A protocol for amide coupling by in situ formation of acyl fluorides and reaction with amines at elevated temperature has been developed and found to be efficient for coupling of sterically hindered substrates and electron deficient amines where standard methods failed.

scholarly journals Ni-Electrocatalytic C(sp3)–C(sp3) Doubly Decarboxylative Coupling

2021 ◽  
Author(s):  
benxiang zhang ◽  
yang gao ◽  
yuta hioki ◽  
martins oderinde ◽  
jennifer qiao ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Present Method ◽  
Bond Formation ◽  
Amide Bond ◽  
Bond Forming ◽  
Amide Bond Formation ◽  
Redox Active ◽  
Decarboxylative Coupling ◽  
The 19Th Century

This work presents a modern spin on one of the oldest known Csp3–Csp3 bond forming reactions in synthetic chemistry: the Kolbe electrolysis. This reaction holds incredible promise for synthesis, yet its use has been near non-existent in mainstream organic synthesis. In contrast to the strongly oxidative electrolytic protocol employed traditionally since the 19th century, the present method utilizes in situ generated redox-active esters (RAEs) which are combined with a mildly reductive Ni-electrocatalytic cycle. It can be used to heterocouple 1o, 2o, and even certain 3o RAEs with a protocol reminiscent of amide bond formation in terms of simplicity. Due to its mild nature the reaction tolerates a range of functional groups, is scalable, and was strategically enlisted for the synthesis of 25 known compounds to reduce overall step-counts by 74%.

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