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Dehydrogenative Meyer–Schuster‐Like Rearrangement: A Gold‐Catalyzed Reaction Generating an Alkyne |
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| Authors: | M?Sc Yang Yu M?Sc Weibo Yang M?Sc Daniel Pflästerer Prof?Dr A Stephen K Hashmi |
| Institution: | 1. Organisch‐Chemisches Institut, Ruprecht‐Karls‐Universit?t Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany) http://www.hashmi.de;2. Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah 21589 (Saudi Arabia) |
| Abstract: | Easily accessible propargylic esters are converted to the inverted alkynyl ketones in an oxidative gold‐catalyzed reaction. Gagosz’s catalyst in combination with PhI(OAc)2 is the best system for this conversion and 18 examples with yields up to 80 % are reported. The results indicate that the triple bond in the product is formed by elimination from a vinylgold intermediate. In a formal sense the new conversion overall is a dehydrogenative Meyer–Schuster rearrangement. |
| Keywords: | alkynes allenes esters gold hypervalent iodine |