18685-03-5Relevant articles and documents
Pd-Senphos Catalyzed trans-Selective Cyanoboration of 1,3-Enynes
Li, Bo,Liu, Shih-Yuan,Zhang, Yuanzhe
supporting information, p. 15928 - 15932 (2020/07/24)
The first trans-selective cyanoboration reaction of an alkyne, specifically a 1,3-enyne, is described. The reported palladium-catalyzed cyanoboration of 1,3-enynes is site-, regio-, and diastereoselective, and is uniquely enabled by the 1,4-azaborine-based Senphos ligand structure. Tetra-substituted alkenyl nitriles are obtained providing useful boron-dienenitrile building blocks that can be further functionalized. The utility of our method has been demonstrated with the synthesis of Satigrel, an anti-platelet aggregating agent.
Synthesis of 1,5-diphenylpent-3-en-1-yne derivatives utilizing an aqueous B-alkyl Suzuki cross coupling reaction
Chuang, Da-Wei,El-Shazly, Mohamed,Chen, Chin-Chau,Chung, Yu-Ming,D. Barve, Balaji,Wu, Ming-Jung,Chang, Fang-Rong,Wu, Yang-Chang
supporting information, p. 5162 - 5166 (2013/09/02)
1,5-Diphenylpent-3-en-1-yne derivatives were isolated in minor quantities from terrestrial plants and exhibited strong anti-inflammatory activity. A cross coupling reaction between B-benzyl-9-BBN and chloroenynes under mild condition was developed resulti
Highly efficient and selective synthesis of conjugated triynes and higher oligoynes of biological and materials chemical interest via palladium-catalyzed alkynyl-alkenyl coupling
Metay, Estelle,Hu, Qian,Negishi, Ei-Ichi
, p. 5773 - 5776 (2007/10/03)
(Diagram presented) Iteration of a Pd-catalyzed reaction of alkynyl- and oligoynylzincs with (E)-ICH=CHCl followed by metalation-termination with electrophiles(E) has provided a linear route to conjugated tri- and tetraynes, and Pd-catalyzed monoalkynylation of 1,1-dibromoenynes accompanied by dehydrobromination has provided a convergent route to conjugated tri-, tetra-, and pentaynes. Both display unprecedented high efficiency and selectivity.
A modular approach to α-arylated carbonyl compounds via indium tris(bistriflylamide)-catalyzed regioselective addition of β-ketoesters to 1,3-diynes
Nakamura, Masaharu,Endo, Kohei,Nakamura, Eiichi
, p. 1681 - 1686 (2007/10/03)
A modular synthesis of α-arylated carbonyl compounds has been achieved by the combination of an indium-catalyzed regioselective addition of β-keto esters to conjugated diynes and a palladium-catalyzed benzannulation reaction. Indium tris(bistriflylamide),
A strictly "pair"-selective synthesis of conjugated diynes via Pd-catalyzed cross coupling of 1,3-diynylzincs: A superior alternative to the Cadiot-Chodkiewicz reaction
Negishi, Ei-Ichi,Hata, Mitsuhiro,Xu, Caiding
, p. 3687 - 3689 (2007/10/03)
(matrix presented) A strictly "pair"-selective synthesis of conjugated diynes via Pd-catalyzed cross coupling of 1,3-diynylzincs is described. This method, like the Cadiot-Chodkiewicz reaction, requires three steps for the synthesis of R1C≡CC≡CR2 from R1C≡CH, R2X, and HC≡CH. However, the high "pair"-selectivity permitting high-yield production of the desired conjugated diynes without separation of symmetrical diynes promises to make the present protocol superior to the Cadiot-Chodkiewicz reaction in many cases.
Convenient one-pot synthesis of functionalized unsymmetrical (Z) or (E)-enediynes from (Z) or (E)-1,2-dichloroethylene. An efficient route to (Z,Z,Z) and (Z,E,Z)-trienes
Alami, Mouad,Crousse, Benoit,Linstrumelle, Gerard
, p. 3543 - 3544 (2007/10/02)
A variety of functionalized unsymmetrical (Z) or (E)-enediynes 1 and 2 are stereospecifically prepared in good overall yield by a simple straightforward one-pot procedure from (Z) or (E)-1,2-dichloroethylene and 1-alkynes. Zinc reduction of 1 and 2 leads
