61766-63-0Relevant articles and documents
Selective Alkynylallylation of the C?C σ Bond of Cyclopropenes
Chen, Ying-Chun,Jiang, Zeqi,Niu, Sheng-Li,Ouyang, Qin,Xiao, Qing,Zeng, Qiang
supporting information, p. 297 - 303 (2020/11/30)
A Pd-catalyzed regio- and stereoselective alkynylallylation of a specific C?C σ bond in cyclopropenes, using allyl propiolates as both allylation and alkynylation reagents, has been achieved for the first time. By merging selective C(sp2)-C(sp3) bond scission with conjunctive cross-couplings, this decarboxylative reorganization reaction features fascinating atom and step economy and provides an efficient approach to highly functionalized dienynes from readily available substrates. Without further optimization, gram-scale products can be easily obtained by such a simple, neutral, and low-cost catalytic system with high TONs. DFT calculations afford a rationale toward the formation of the products and indicate that the selective insertion of the double bond of cyclopropenes into the C-Pd bond of ambidentate Pd complex and the subsequent nonclassical β-C elimination promoted by 1,4-palladium migration are critical for the success of the reaction.
Gold-catalyzed oxidative couplings of two indoles with one aryldiazo cyanide under oxidant-free conditions
Singh, Rahulkumar Rajmani,Liu, Rai-Shung
supporting information, p. 4593 - 4596 (2017/04/28)
Gold-catalyzed oxidative couplings of two indoles and one α-cyano gold carbene to form bis(indolyl)methane derivatives are described. Two different indoles are compatible with these reactions to provide reasonable yields. A plausible mechanism is postulated to rationalize the experimental data including product distributions, D2O labeling, and the significant effects of gold catalysts and cyano groups.
Gold-Catalyzed Oxidative [2+2+1] Annulations of Aryldiazo Nitriles with Imines To Yield Polyarylated Imidazolium Salts
Pawar, Samir Kundlik,Yang, Ming-Chung,Su, Ming-Der,Liu, Rai-Shung
supporting information, p. 5035 - 5039 (2017/04/24)
Gold-catalyzed oxidative [2+2+1] annulations between two imines and one α-cyano arylgold carbene afforded polyarylated imidazolium salts and molecular hydrogen efficiently. Control experiments suggest that the gold catalyst alone facilitates the main annulation, whereas Ag+ avoids the formation of inactive LAuCN. DFT calculations suggest that the success of this annulation relies on a 6 π-electrocyclization of cyano-free intermediates with cis-configured imines as initial reagents.
Gold-catalyzed [3+2]-annulations of α-aryl diazonitriles with ynamides and allenamides to yield 1-amino-1H-indenes
Singh, Rahulkumar Rajmani,Pawar, Samir Kundlik,Huang, Min-Jie,Liu, Rai-Shung
, p. 11434 - 11437 (2016/09/23)
Gold-catalyzed [3+2]-annulations of α-aryl diazonitriles with ynamides and allenamides yield 1-amino-1H-indenes in two distinct pathways; the success of these annulations relies on the high electrophilicity of α-cyano arylgold carbenes to activate an ionic pathway.
Triplet photochemistry of acyl and imino cyclopropenes. a rearrangement to afford furans and pyrroles: Reaction and mechanism
Zimmerman, Howard E.,Wright, Charles W.
, p. 6603 - 6612 (2007/10/02)
Syntheses of 3-substituted 3-acylcyclopropenes and 3-benzoylcyclopropene imines were devised. A triplet rearrangement of acylcyclopropenes having C-3 aryl substitution to afford furans has been uncovered and studied with several examples. Unlike the singl
