3199-62-0Relevant articles and documents
Palladium complexes with an annellated mesoionic carbene (MIC) ligand: Catalytic sequential Sonogashira coupling/cyclization reaction for one-pot synthesis of benzofuran, indole, isocoumarin and isoquinolone derivatives
Bera, Jitendra K.,Daw, Prosenjit,Reshi, Noor U Din,Tyagi, Akshi
, p. 15238 - 15248 (2020)
Two Pd(ii) complexes (1 and 2) featuring a fused π-conjugated imidazo[1,2-a][1,8]naphthyridine-based mesoionic carbene ligand have been synthesized and structurally characterized. Both complexes effectively catalyze the one-pot synthesis of benzofuran starting from phenylacetylene and 2-iodophenol under mild conditions. Complex 1 is found to be an excellent catalyst for the straightforward access to a library of benzofuran, indole, isocoumarin and isoquinolone derivatives by the reaction of terminal alkynes with 2-iodo derivates of phenol, N-methyl aniline, benzoic acid and N-methyl benzamide, respectively. The general utility of the catalytic method is demonstrated using a variety of diversely substituted terminal alkynes and the corresponding desired products are obtained in good to excellent yields. On the basis of control experiments, a two-cycle mechanism is proposed which involves the Sonogashira coupling of 2-iodo derivatives with alkynes and the subsequent cyclization of the corresponding 2-alkynyl compounds.
Dual Cobalt and Photoredox Catalysis Enabled Redox-Neutral Annulation of 2-Propynolphenols
Ding, Hai-Xin,He, Yong-Qin,Song, Xian-Rong,Tian, Wan-Fa,Wang, Mei,Xiao, Qiang,Zhou, Zhao-Zhao,Zhu, Yao
, p. 3372 - 3377 (2021)
A hydroxyl-assisted, organophotoredox/cobalt dual catalyzed annulation of 2-propynolphenols to form 2-hydroxymethyl-benzo[b]furans was developed by employing 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) as photosensitizer and CoCl2/su
Cooperation of Mn(III)/Br?nsted acid for the synthesis of quindoline derivatives via dehydroxylation/azidation/cyclization cascade of diaryl(1 H-indol-2-yl)methanols with trimethylsilyl azide
Zhou, Yu,Xu, Xiao-Ping,Ji, Shun-Jun
supporting information, p. 2039 - 2042 (2019/04/10)
A new synthesis of quindoline derivatives promoted by Mn(III)/Br?nsted acid via a dehydroxylation/azidation/cyclization cascade of diaryl(1H-indol-2-yl)methanols with trimethylsilyl azide was developed. The reaction features very effective transformation involving two C(sp2)-H and one C(sp3)-O bond cleavages, two C(sp2)-N bonds, and one N-heterocycle formation in a one-pot manner. A series of 11-arylquindolines were synthesized in good yields.
Organocatalytic deprotonative functionalization of C(sp2)-H and C(sp3)-H bonds using in situ generated onium amide bases
Inamoto, Kiyofumi,Okawa, Hitomi,Taneda, Hiroshi,Sato, Maomi,Hirono, Yutaro,Yonemoto, Misato,Kikkawa, Shoko,Kondo, Yoshinori
supporting information, p. 9771 - 9773,3 (2020/08/31)
Onium amides, generated in situ from the combination of aminosilanes and onium fluorides (R4PF, R4NF), are employed for the first time as bases for catalytic deprotonative functionalization of C(sp 2)-H and activated C(sp
Deprotonation of furans using lithium magnesates
Mongin, Florence,Bucher, Aurélien,Bazureau, Jean Pierre,Bayh, Omar,Awad, Ha?an,Trécourt, Fran?ois
, p. 7989 - 7992 (2007/10/03)
Furan was deprotonated on treatment with 1/3 equiv of Bu3MgLi in THF at rt. The lithium arylmagnesate formed was either trapped with electrophiles or involved in a palladium-catalyzed cross-coupling reaction with 2-bromopyridine. The highly coordinated magnesate Bu4MgLi2 (1/3 equiv) proved to be a better deprotonating agent than Bu3MgLi; the monitoring of the reaction using NMR spectroscopy showed that the deprotonation of furan at rt required 2 h whereas the subsequent electrophilic trapping was instantaneous. The method was extended to benzofuran, allowing its functionalization at C2 in high yields. The deprotonation of 2-methylfuran and lithium furfurylalkoxide at C5 turned out to be difficult, requiring either long reaction times or higher temperatures.
