Stereoselective Synthesis of Trisubstituted (E,E)-1,3-Dienes by the Site-Selective Reductive Cross-Coupling of Internal Alkynes with Terminal Alkynes: A Fragment Coupling Reaction for Natural Product Synthesis

2009 ◽  
Vol 74 (19) ◽  
pp. 7211-7219 ◽  
Author(s):  
Lark J. Perez ◽  
Heidi L. Shimp ◽  
Glenn C. Micalizio
Keyword(s):  
Natural Product ◽  
Stereoselective Synthesis ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Natural Product Synthesis ◽  
Terminal Alkynes ◽  
Internal Alkynes ◽  
Site Selective

Stereoselective Synthesis of Coreoside D and Determination of Its Absolute Configuration

Synlett ◽  
2020 ◽  
Vol 31 (14) ◽  
pp. 1409-1412
Author(s):  
Narihito Ogawa ◽  
Ryoya Imaizumi
Keyword(s):  
Natural Product ◽  
Absolute Configuration ◽  
Stereoselective Synthesis ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
D Values ◽  
Glycosylation Reaction

We report the stereoselective synthesis of (3S)- and (3R)-coreoside D. The conjugated diyne in the C1–C14 moiety was synthesized through two types of palladium-catalyzed cross-coupling reaction. The introduction of the glucopyranose was achieved by a glycosylation reaction using an imidate derivative in the presence of a Lewis acid. The asymmetric center at the C3-position was constructed by the chiral-pool method using d-malic acid. The stereochemistry at the C3-position of the natural product was determined to be R by comparing the [α]D values of the synthetic stereoisomers with that reported for the natural product.

Direct Site-Selective Arylation of Enamides via a Decarboxylative Cross-Coupling Reaction

2013 ◽  
Vol 15 (4) ◽  
pp. 816-819 ◽  
Author(s):  
Nicolas Gigant ◽  
Laëtitia Chausset-Boissarie ◽  
Isabelle Gillaizeau
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Cross Coupling Reaction ◽  
Site Selective

Palladium Catalyzed Synthesis of Phenylquinoxaline-Alkyne Derivatives via Sonogashira Cross Coupling Reaction

2021 ◽  
Vol 43 (1) ◽  
pp. 95-95
Author(s):  
Rifhat Bibi Rifhat Bibi ◽  
Muhammad Yaseen Muhammad Yaseen ◽  
Haseen Ahmad Haseen Ahmad ◽  
Ismat Ullah Khan Ismat Ullah Khan ◽  
Shaista Parveen Shaista Parveen ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Sonogashira Reaction ◽  
Terminal Alkynes ◽  
Vinyl Halides ◽  
Sonogashira Coupling Reaction ◽  
Quinoxaline Derivatives ◽  
Palladium Catalyzed ◽  
High Yields ◽  
Alkyne Derivatives

Transition metals mediated cross coupling methodologies provide an extremely powerful versatile pathway in organic syntheses undoubtedly, a facile route for syntheses and derivatization of biologically important heterocycles from easily available precursors. Sonogashira coupling reaction, a leading method to Csp-Csp2 bond formation is one of the most important and rapid pathways to couple aryl/vinyl halides with terminal alkynes. Current research study deals with the synthesis of alkyne substituted quinoxaline derivatives. The quinoxalines class of aromatic heterocycles exhibits a wide variety of important biological potencies. Palladium catalyzed cross coupling process provided an effective synthetic practice for the synthesis of alkyne derivatives of quinoxaline. Vareity of terminal alkynes were coupled with 2-(4-bromophenyl)quinoxaline under optimized conditions for Sonogashira reaction, affording alkyne substituted quinoxaline derivatives in high yields. The optimized reaction conditions for coupling of range of terminal alkyne with quinoxaline basic core render this process significant for designing of medicinally interesting precursors.

Palladium-catalyzed denitrative Sonogashira-type cross-coupling of nitrobenzenes with terminal alkynes

2020 ◽  
Vol 56 (5) ◽  
pp. 790-793 ◽  
Author(s):  
Boya Feng ◽  
Yudong Yang ◽  
Jingsong You
Keyword(s):  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Terminal Alkynes ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed

Described herein is a palladium-catalyzed cross-coupling reaction between nitroarenes and terminal alkynes, offering a facile method for C(sp2)–C(sp) bond formation.

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