Metal and carbene organocatalytic relay activation of alkynes for stereoselective reactions

Kayambu Namitharan, Tingshun Zhu, Jiajia Cheng, Pengcheng Zheng, Xiangyang Li, Song Yang, Bao-An Song () and Yonggui Robin Chi ()
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Kayambu Namitharan: School of Physical and Mathematical Sciences, Nanyang Technological University
Tingshun Zhu: School of Physical and Mathematical Sciences, Nanyang Technological University
Jiajia Cheng: School of Physical and Mathematical Sciences, Nanyang Technological University
Pengcheng Zheng: School of Physical and Mathematical Sciences, Nanyang Technological University
Xiangyang Li: Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China
Song Yang: Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China
Bao-An Song: Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China
Yonggui Robin Chi: School of Physical and Mathematical Sciences, Nanyang Technological University

Nature Communications, 2014, vol. 5, issue 1, 1-7

Abstract: Abstract Transition metal and organic catalysts have established their own domains of excellence. It has been expected that merging the two unique domains should provide complimentary or unprecedented opportunities in converting simple raw materials to functional products. N-heterocyclic carbenes alone are excellent organocatalysts. When used with transition metals such as copper, N-heterocyclic carbenes are routinely practiced as strong-coordinating ligands. Combination of an N-heterocyclic carbene and copper therefore typically leads to deactivation of either or both of the two catalysts. Here we disclose the direct merge of copper as a metal catalyst and N-heterocyclic carbenes as an organocatalyst for relay activation of alkynes. The reaction involves copper-catalysed activation of alkynes to generate ketenimine intermediates that are subsequently activated by an N-heterocyclic carbene organocatalyst for stereoselective reactions. Each of the two catalysts (copper metal catalyst and N-heterocyclic carbene organocatalyst) accomplishes its own missions in the activation steps without quenching each other.

Date: 2014
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DOI: 10.1038/ncomms4982

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