85437-89-4Relevant academic research and scientific papers
Semireduction of alkynoic acids via a transition metal-free α borylation-protodeborylation sequence
Verma, Astha,Grams, R. Justin,Rastatter, Brett P.,Santos, Webster L.
, p. 2113 - 2117 (2019)
A method for the semi-reduction of alkynoic acids through an α-borylation and subsequent protodeborylation mechanism has been developed. The transition metal-free protocol is achieved through the activation of bis(pinacolato)diboron by an in situ generated carboxylate moiety yielding aryl acrylic acids. Our studies demonstrate an unprecedented dual role for the carboxylate anion that involves the activation of the diboron reagent and a directing effect in the α-borylation.
Key structural features of cis-cinnamic acid as an allelochemical
Abe, Masato,Nishikawa, Keisuke,Okuda, Katsuhiro,Shindo, Mitsuru,Fukuda, Hiroshi,Nakanishi, Kazunari,Tazawa, Yuta,Taniguchi, Tomoya,Park, So-Young,Hiradate, Syuntaro,Fujii, Yoshiharu
, p. 56 - 67,12 (2012/12/12)
1-O-cis-cinnamoyl-β-d-glucopyranose is one of the most potent allelochemicals isolated from Spiraea thunbergii Sieb. It is suggested that it derives its strong inhibitory activity from cis-cinnamic acid, which is crucial for phytotoxicity. It was synthesized to confirm its structure and bioactivity, and also a series of cis-cinnamic acid analogues were prepared to elucidate the key features of cis-cinnamic acid for lettuce root growth inhibition. The cis-cyclopropyl analogue showed potent inhibitory activity while the saturated and alkyne analogues proved to be inactive, demonstrating the importance of the cis-double bond. Moreover, the aromatic ring could not be replaced with a saturated ring. However, the 1,3-dienylcyclohexene analogue showed strong activity. These results suggest that the geometry of the C-C double bond between the carboxyl group and the aromatic ring is essential for potent inhibitory activity. In addition, using several light sources, the photostability of the cinnamic acid derivatives and the role of the C-C double bond were also investigated.
VINYL COPPER REAGENTS-16. SYNTHESIS OF CONJUGATED DIENES VIA THE ADDITION OF VINYL CUPRATES TO ACETYLENE
Alexakis, A.,Normant, J. F.
, p. 5151 - 5154 (2007/10/02)
Some alkenyl cuprates add smoothly to acetylene yielding dienyl cuprates.
