2014
DOI: 10.1002/hc.21184
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Zwitterionic Phosphirenium Borates Derived from Bis(alkynyl)mesityl Phosphanes and Tris(pentafluorophenyl)borane

Abstract: From a series of bis(alkynyl)mesityl phosphanes 5, we prepared phosphirenium borate compounds 6 in high yields by reaction with B(C6F5)3 at room temperature. The zwitterionic compounds 6 are conveniently accessible and can be obtained with unique substitution patterns by this route. For two examples, we show the conversion of 6 to the respective 3‐borylated phosphole derivatives 7 through multiple 1,1‐carboboration reactions. In a useful one‐pot methodology, the phosphirenium borates 6 are converted to air‐sta… Show more

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Cited by 14 publications
(4 citation statements)
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“…Thermolysis of the phosphirenium borates resulted in the formation of the 1,1-carboboration products 6-8-2 or phospholes 6-8-3. [298][299][300][301][302][303][304][305] In 2016, Erker and co-workers demonstrated the reaction of allene 6-9-1 with Piers' borane, HB(C6F5)2 to give zwitterionic phosphonium borate a3CP13 (Scheme 6-9). 306 Heating of a3CP13 for 6 days in toluene at 110 °C underwent internal nucleophilic aromatic substitution to form 6-9-2.…”
Section: Snmentioning
confidence: 99%
“…Thermolysis of the phosphirenium borates resulted in the formation of the 1,1-carboboration products 6-8-2 or phospholes 6-8-3. [298][299][300][301][302][303][304][305] In 2016, Erker and co-workers demonstrated the reaction of allene 6-9-1 with Piers' borane, HB(C6F5)2 to give zwitterionic phosphonium borate a3CP13 (Scheme 6-9). 306 Heating of a3CP13 for 6 days in toluene at 110 °C underwent internal nucleophilic aromatic substitution to form 6-9-2.…”
Section: Snmentioning
confidence: 99%
“…The reaction of 7a and 7b took a different course than the one with 7c . Both alkynyl groups in the systems 7 bear substituents at their ends that have previously been shown to serve as good migrating groups in 1,1-carbo­boration reactions. , In the systems 7a and 7b , the PAr 2 substituents became the favored migrating groups under our typical reaction conditions. We isolated the products 8a and 8b formed by selective 1,1-carbo­boration at the respective CC-PAr 2 moiety in good yields.…”
Section: Resultsmentioning
confidence: 99%
“…At slightly elevated temperatures the corresponding boryl substituted phospholes 49 were obtained in good yields (see Scheme 13 ). 38 The reaction course was followed by temperature dependent 31 P NMR spectroscopy. In this way we were able to observe some intermediates of the typical sequential 1,1-carboboration pathway along the way ranging from initial phosphane/borane adduct formation through the stages of the phosphirenium/borate zwitterion formation followed by the 1,1-carboboration product isomers at the first alkynyl unit, all the way to the final phosphole products.…”
Section: Five-membered Heterocycles By 11-carboborationmentioning
confidence: 99%