173019-85-7Relevant articles and documents
Regioselective Iron-Catalysed Cross-Coupling Reaction of Aryl Propargylic Bromides and Aryl Grignard Reagents
Manjón-Mata, Inés,Quirós, M. Teresa,Bu?uel, Elena,Cárdenas, Diego J.
supporting information, p. 146 - 151 (2019/12/11)
An iron-catalysed Kumada-type cross-coupling reaction between aryl substituted propargylic bromides and arylmagnesium reagents has been developed. Propargylic coupling products were the main or only outcome, and propargyl/allene regioselectivity was shown to depend on the electronic nature of the substituents on the triple bond of the substrate and on the arylmagnesium halide. Best selectivities were observed when electron donating substituents were present in either reagent. The process is stereoespecific, occurs with configuration inversion and no carbon-based radicals seem to be involved in the mechanism. (Figure presented.).
Direct Access to Allenylphosphine Oxides via a Metal Free Coupling of Propargylic Substrates with P(O)H Compounds
Yang, Chun-Hua,Fan, Huihui,Li, Huimin,Hou, Shenyin,Sun, Xiangkun,Luo, Donghao,Zhang, Yinchao,Yang, Zhantao,Chang, Junbiao
supporting information, p. 9438 - 9441 (2019/11/20)
A direct and convenient approach for the coupling of propargylic substrates with diphenylphosphine oxide in the presence of Tf2O and 2,6-lutidine has been developed. The method provides a general approach for the construction of attractive allenylphosphoryl skeletons with high atom and step economy under metal free conditions.
Iron-Catalyzed Coupling of Propargyl Bromides and Alkyl Grignard Reagents
Domingo-Legarda, Pablo,Soler-Yanes, Rita,Quirós-López, M. Teresa,Bu?uel, Elena,Cárdenas, Diego J.
supporting information, p. 4900 - 4904 (2018/09/10)
An iron-catalyzed Kumada-type cross-coupling reaction of propargyl halides with alkylmagnesium reagents is described. The reaction is fast, takes place in smooth conditions, tolerates several functional groups that would be able to react with the Grignard reagent, and may afford either allene or propargyl coupling derivatives. Factors involved in the observed regioselectivity have been studied.