1‐Bromo‐2‐(cyclopropylidenemethyl)benzene: A Useful Building Block in the Palladium‐Catalyzed Reaction of 2‐Alkynylbenzenamine

2012 ◽  
Vol 7 (7) ◽  
pp. 1691-1696 ◽  
Author(s):  
Shaoyu Li ◽  
Yong Luo ◽  
Xiaocong Wang ◽  
Minjie Guo ◽  
Jie Wu
Keyword(s):  
Building Block ◽  
Palladium Catalyzed

scholarly journals Efficient and Reproducible Synthesis of an Fmoc-protected Tn Antigen

2021 ◽  
Author(s):  
Michael R. Reynolds ◽  
Sabrina Piazza ◽  
Jonathan Chiaramonte ◽  
Fabiola A. Chapa-Villarreal ◽  
John Trant
Keyword(s):  
Total Synthesis ◽  
Peptide Synthesis ◽  
Building Block ◽  
Large Scale ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Tn Antigen ◽  
Palladium Catalyzed ◽  
Glycosyl Donor ◽  
Antigen A

The total synthesis of the Thomsen-nouveau (Tn) antigen, a tumour-associated O-linked mucin glycopeptide, was achieved through a concise route. The key glycosylation step proved challenging to reproduce from the literature precedents and was most reliably accomplished using a palladium-catalyzed coupling between the glycosyl donor and Fmoc-functionalized serine acceptor to form the target in moderate yields. This is, to the best of our knowledge, the shortest synthesis reported from galactose for preparing this essential building block for large-scale solid phase peptide synthesis.

Bicyclopropylidene. A unique tetrasubstituted alkene and versatile C6-building block for organic synthesis

2000 ◽  
Vol 72 (9) ◽  
pp. 1745-1756 ◽  
Author(s):  
Gary A. Molander
Keyword(s):  
Double Bond ◽  
Organic Synthesis ◽  
Building Block ◽  
Aryl Halides ◽  
Polymer Support ◽  
Additional Dimension ◽  
Palladium Catalyzed ◽  
Cleavage Step ◽  
Combinatorial Sense ◽  
Single Bonds

Bicyclopropylidene (4), now readily available in preparatively viable quantities, is evolving as a useful C6 building block for organic synthesis due to its enhanced reactivity at the C-H, the C=C, as well as both types of C-C single bonds. Monosubstituted derivatives are accessible by deprotonation/electrophilic substitution. Di- and tetrasubstituted bicyclopropylidenes are best made by copper-mediated reductive dimerization of bromolithiocarbenoids. The 1,3-dipolar cycloadducts of nitrones rearrange to spirocyclopropanated piperidones, palladium-catalyzed codimerizations with acrylates occur with opening of one of the rings to yield precursors to bicyclo[3.3.0]octene and bicyclo[5.3.0]decene skeletons. Silicon-heteroatom bonds can be added across the double bond of 4 under palladium catalysisjust like across a C텡C triple bond, and carbopalladation of the double bond in 4 occurs more rapidly than that in an acrylate. A variety of new three-component reactions of 4 with alkenyl as well as aryl halides and dienophiles have been developed and extended to be carried out in a combinatorial sense, even on a polymer support, with an additional dimension added in the cleavage step. Most of the reported reactions of bicyclopropylidene (4) proceed with good to excellent yields.

Carbon dioxide as a C1 building block. Mechanism of palladium-catalyzed carboxylation of aromatic halides

1992 ◽  
Vol 114 (18) ◽  
pp. 7076-7085 ◽  
Author(s):  
Christian Amatore ◽  
Anny Jutand ◽  
Fouad Khalil ◽  
Merete F. Nielsen
Keyword(s):  
Carbon Dioxide ◽  
Building Block ◽  
Palladium Catalyzed ◽  
Block Mechanism
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