Pd-catalyzed Oxidative Cyclization of Bromoalkynes with N-AllylaminesA Strategy to 3-Bromosubstitute

来源 :第五届岭南有机化学论坛暨华南理工大学-兰州大学有机化学双边论坛 | 被引量 : 0次 | 上传用户:jinr0op4
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Pyrrole skeleton represents an interesting class of nitrogen-containing heterocycles,which frequently occurs in naturally and synthetically bioactive products as well as top-sold marketing medicines.1 Therefore,the development of efficient methods to access these privileged molecules is of significant importance.Meanwhile,3-halosubsituted pyrroles provide a facile route for the derivatization at the 3-position of pyrroles since there are only limited reports on the selective functionalization of the C-3 position of pyrroles.2 However,the examples of the synthesis of 3-halo-substituted pyrroles are still very rare.3 On the other hand,retaining the halide moiety in the reaction of haloalkynes is still a challenge,which makes these protocols more atom-economic.As our continuous interest in developing novel and practical synthetic methods based on haloalkyne reagents,4 herein,we report a Pd-catalyzed oxidative cyclization to access various 3-bromopyrroles in a single operation.In this strategy,only two hydrogen atoms are removed,the retained bromine atom makes further functionalizations possible at the 3-position of pyrroles.
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