Palladium-catalyzed decarboxylative gem-selective addition of alkynoic acids to terminal alkynes

2020 ◽  
Vol 7 (23) ◽  
pp. 3918-3925
Author(s):  
Hyojin Jeon ◽  
Soo-Byung Ko ◽  
Sunwoo Lee
Keyword(s):  
High Selectivity ◽  
Terminal Alkynes ◽  
Palladium Catalyzed ◽  
Propiolic Acid ◽  
Selective Addition

Alkynoic acids added to terminal alkynes to give gem-1,3-enynes with high selectivity and good yields. In addition, the reaction of alkynoic acids with propiolic acid provided the corresponding gem-1,3-enynes via double decarboxylation.

Formal Total Syntheses of Crocacin A-D

2005 ◽  
Vol 70 (10) ◽  
pp. 1696-1708 ◽  
Author(s):  
Magnus Besev ◽  
Christof Brehm ◽  
Alois Fürstner
Keyword(s):  
Natural Products ◽  
Aldol Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Total Syntheses ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
The Common ◽  
Selective Addition

A concise route to the common polyketide fragment5of crocacin A-D (1-4) is presented which has previously been converted into all members of this fungicidal and cytotoxic family of dipeptidic natural products by various means. Our synthesis features asyn-selective titanium aldol reaction controlled by a valinol-derived auxiliary, a zinc-mediated, palladium-catalyzedanti-selective addition of propargyl mesylate10to the chiral aldehyde9, as well as a comparison of palladium-catalyzed Stille and Suzuki cross-coupling reactions for the formation of the diene moiety of the target.

ChemInform Abstract: Palladium-Catalyzed Aryloxycarbonylation of Terminal Alkynes.

ChemInform ◽  
2010 ◽  
Vol 24 (4) ◽  
pp. no-no
Author(s):  
K. ITOH ◽  
M. MIURA ◽  
M. NOMURA
Keyword(s):  
Terminal Alkynes ◽  
Palladium Catalyzed

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.

scholarly journals C–C (alkynylation) vs C–O (ether) bond formation under Pd/C–Cu catalysis: synthesis and pharmacological evaluation of 4-alkynylthieno[2,3-d]pyrimidines

2011 ◽  
Vol 7 ◽  
pp. 338-345 ◽  
Author(s):  
Dhilli Rao Gorja ◽  
K Shiva Kumar ◽  
K Mukkanti ◽  
Manojit Pal
Keyword(s):  
Cytotoxic Activity ◽  
Catalytic System ◽  
High Selectivity ◽  
Bond Formation ◽  
Terminal Alkynes ◽  
Ether Bond ◽  
Pharmacological Evaluation

The Pd/C–CuI–PPh3 catalytic system facilitated C–C bond formation between 4-chlorothieno[2,3-d]pyrimidines and terminal alkynes in methanol with high selectivity without generating any significant side products arising from C–O bond formation between the chloro compounds and methanol. A variety of novel 4-alkynylthieno[2,3- d]pyrimidines were prepared via alkynylation of 4-chlorothieno[2,3-d]pyrimidines in good to excellent yields. Some of the compounds synthesized were tested for cytotoxic activity in vitro.

Synthesis of Ynones by Palladium-Catalyzed Acylation of Terminal Alkynes with Acid Chlorides

2004 ◽  
Vol 69 (5) ◽  
pp. 1615-1619 ◽  
Author(s):  
Diego A. Alonso ◽  
Carmen Nájera ◽  
M Carmen Pacheco
Keyword(s):  
Terminal Alkynes ◽  
Acid Chlorides ◽  
Palladium Catalyzed

Oxidative Cross-Coupling through Double Transmetallation:  Surprisingly High Selectivity for Palladium-Catalyzed Cross-Coupling of Alkylzinc and Alkynylstannanes

2006 ◽  
Vol 128 (47) ◽  
pp. 15048-15049 ◽  
Author(s):  
Yingsheng Zhao ◽  
Haibo Wang ◽  
Xiaohui Hou ◽  
Yanhe Hu ◽  
Aiwen Lei ◽  
...  
Keyword(s):  
High Selectivity ◽  
Cross Coupling ◽  
Palladium Catalyzed

ChemInform Abstract: Palladium-Catalyzed Addition of Silyl-Substituted Chloroalkynes to Terminal Alkynes.

ChemInform ◽  
2010 ◽  
Vol 42 (4) ◽  
pp. no-no
Author(s):  
Tatsuya Wada ◽  
Masayuki Iwasaki ◽  
Azusa Kondoh ◽  
Hideki Yorimitsu ◽  
Koichiro Oshima
Keyword(s):  
Terminal Alkynes ◽  
Palladium Catalyzed
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