{"id":5812,"date":"2021-10-11T11:48:10","date_gmt":"2021-10-11T04:48:10","guid":{"rendered":"http:\/\/chemistry.sc.mahidol.ac.th\/?page_id=5812"},"modified":"2021-10-11T11:48:10","modified_gmt":"2021-10-11T04:48:10","slug":"nickel-mediated-cross-coupling-via-c-o-activation-assisted-by-organoaluminum","status":"publish","type":"page","link":"https:\/\/chemistry.sc.mahidol.ac.th\/nickel-mediated-cross-coupling-via-c-o-activation-assisted-by-organoaluminum\/","title":{"rendered":"Nickel-mediated cross-coupling via C\u2013O activation assisted by organoaluminum"},"content":{"rendered":"\n<p class=\"wp-block-paragraph\">Cheng-Yuan Liu1 | Taveechai Wititsuwannakul2 | Chu-Han Hsieh1,3 | Chung-Yu Tsai1,3 | Ting-Hsuan Wang1 | Ram Ambre1 | Wen-Ching Chen1 | Panida Surawatanawong<em>2,4 | Tiow-Gan Ong<\/em>1,5<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><sup>1<\/sup>Institute of Chemistry, Academia Sinica, Nangang, Taipei, Taiwan, Republic of China<br><sup>2<\/sup>Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahidol<br>University, Bangkok, Thailand<br><sup>3<\/sup>Department of Chemical Engineering, National Taiwan University of Science and Technology, Taipei, Taiwan,<br>Republic of China<br><sup>4<\/sup>Center of Sustainable Energy and Green Materials, Mahidol University, Salaya, Nakhon Pathom, Thailand<br><sup>5<\/sup>The Department of Applied Chemistry, National Chiao-Tung University, Hsinchu, Taiwan, Republic of China<\/p>\n\n\n\n<p class=\"has-text-align-left wp-block-paragraph\">We report the alkylation and arylation cross-coupling of aryl ethers based on C\u2013O bond<br>activation using a nickel catalyst and organoaluminum reagents. Ni(cod)2 in combination with<br>1,2-bis(dicyclohexylphosphino)ethane ligand in toluene solution at 130\u00b0C are the best conditions.<br>The naphthyl ether or methoxy pyridine derivatives are suitable substrates for alkylation and<br>arylation reaction with a wider scope of aluminum reagents in good yields. Computational<br>analysis on the pyridine substrate is provided to help delineate the mechanistic pathway and<br>demonstrate the important aspects of the cooperative interaction bimetallic catalysis. First, the<br>coordination of AlMe3 to the O atom of pyridine is essential for C\u2013O activation. Second, the \u03b2-H<br>transfer from methoxy to pyridine could be discouraged through the use of bidentate phosphine<br>as a ligand. Finally, excess AlMe3 reagent is critical for facilitating a reductive elimination process.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Reference: Liu, C.-Y.; Wititsuwannakul, T.; Hsieh, C.-H.; Tsai, C.-Y.; Wang, T.-H.; Ambre, R.; Chen, W.-C.;<br>Surawatanawong<em>, P.; Ong<\/em>, T.-G. J. Chin. Chem. Soc. 2020, 67, 376-382. https:\/\/doi.org\/10.1002\/jccs.201900450<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Cheng-Yuan Liu1 | Taveechai Wititsuwannakul2 | Chu-Han Hsieh1,3 | Chung-Yu Tsai1,3 | Ting-Hsuan Wang1 | Ram Ambre1 | Wen-Ching Chen1 | Panida Surawatanawong2,4 | Tiow-Gan Ong1,5 1Institute of Chemistry, Academia Sinica, Nangang, Taipei, Taiwan, Republic of China2Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, MahidolUniversity, Bangkok, Thailand3Department of Chemical [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"parent":0,"menu_order":0,"comment_status":"closed","ping_status":"closed","template":"","meta":{"footnotes":""},"class_list":["post-5812","page","type-page","status-publish","hentry"],"_links":{"self":[{"href":"https:\/\/chemistry.sc.mahidol.ac.th\/wp-json\/wp\/v2\/pages\/5812","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/chemistry.sc.mahidol.ac.th\/wp-json\/wp\/v2\/pages"}],"about":[{"href":"https:\/\/chemistry.sc.mahidol.ac.th\/wp-json\/wp\/v2\/types\/page"}],"author":[{"embeddable":true,"href":"https:\/\/chemistry.sc.mahidol.ac.th\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/chemistry.sc.mahidol.ac.th\/wp-json\/wp\/v2\/comments?post=5812"}],"version-history":[{"count":1,"href":"https:\/\/chemistry.sc.mahidol.ac.th\/wp-json\/wp\/v2\/pages\/5812\/revisions"}],"predecessor-version":[{"id":5813,"href":"https:\/\/chemistry.sc.mahidol.ac.th\/wp-json\/wp\/v2\/pages\/5812\/revisions\/5813"}],"wp:attachment":[{"href":"https:\/\/chemistry.sc.mahidol.ac.th\/wp-json\/wp\/v2\/media?parent=5812"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}