Palladium-Catalyzed Allylation of Aryl Halides with Homoallyl Alcohols Bearing a Trisubstituted Double Bond: Application to Chirality Transfer from Hydroxylated Carbon to Benzylic One

2010 ◽  
Vol 75 (13) ◽  
pp. 4337-4343 ◽  
Author(s):  
Ryota Wakabayashi ◽  
Daishi Fujino ◽  
Sayuri Hayashi ◽  
Hideki Yorimitsu ◽  
Koichiro Oshima
Keyword(s):  
Double Bond ◽  
Aryl Halides ◽  
Chirality Transfer ◽  
Trisubstituted Double Bond ◽  
Palladium Catalyzed

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.

scholarly journals Synthesis of (+)-solenopsin via Pd-catalyzed N-alkylation and cyclization

2021 ◽  
Vol 85 (2) ◽  
pp. 223-227
Author(s):  
Kana Suzuki ◽  
Yasunao Hattori ◽  
Atsushi Kawamura ◽  
Hidefumi Makabe
Keyword(s):  
Double Bond ◽  
Fire Ants ◽  
Chain Elongation ◽  
Piperidine Ring ◽  
Palladium Catalyzed

ABSTRACT Synthesis of (+)-solenopsin, a 2,6-disubstituted piperidine alkaloid, isolated from fire ants (Solenopsis), was achieved. Stereoselective construction of trans-2,6-piperidine ring moiety was performed using palladium-catalyzed cyclization. Chain elongation using Grubbs 2nd catalyst followed by the reduction of double bond and the deprotection of the Cbz group afforded (+)-solenopsin.

Palladium Catalyzed Cascade Azidation/Carbonylation of Aryl Halides with Sodium Azide for the Synthesis of Amides

2021 ◽  
Author(s):  
Zhuang Qi ◽  
Shan‐Shan Li ◽  
Lin Li ◽  
Qi Qin ◽  
Li‐Miao Yang ◽  
...  
Keyword(s):  
Sodium Azide ◽  
Aryl Halides ◽  
Palladium Catalyzed

Palladium-Catalyzed Olefinations of Aryl Halides (Heck Reaction) and Related Transformations

ChemInform ◽  
2005 ◽  
Vol 36 (44) ◽  
Author(s):  
Matthias Beller ◽  
Alexander Zapf ◽  
Thomas H. Riermeier
Keyword(s):  
Heck Reaction ◽  
Aryl Halides ◽  
Palladium Catalyzed

ChemInform Abstract: A General and Efficient Catalyst for Palladium-Catalyzed C-O Coupling Reactions of Aryl Halides with Primary Alcohols.

ChemInform ◽  
2010 ◽  
Vol 42 (4) ◽  
pp. no-no
Author(s):  
Saravanan Gowrisankar ◽  
Alexey G. Sergeev ◽  
Pazhamalai Anbarasan ◽  
Anke Spannenberg ◽  
Helfried Neumann ◽  
...  
Keyword(s):  
Aryl Halides ◽  
Coupling Reactions ◽  
Primary Alcohols ◽  
Efficient Catalyst ◽  
Palladium Catalyzed
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