{"main_file_link":[{"url":"https://doi.org/10.1021/acscatal.3c02977","open_access":"1"}],"extern":"1","OA_type":"hybrid","article_processing_charge":"Yes (in subscription journal)","status":"public","citation":{"apa":"Reisenbauer, J., Finkelstein, P., Ebert, M.-O., &#38; Morandi, B. (2023). Mechanistic investigation of the nickel-catalyzed transfer hydrocyanation of alkynes. <i>ACS Catalysis</i>. American Chemical Society. <a href=\"https://doi.org/10.1021/acscatal.3c02977\">https://doi.org/10.1021/acscatal.3c02977</a>","chicago":"Reisenbauer, Julia, Patrick Finkelstein, Marc-Olivier Ebert, and Bill Morandi. “Mechanistic Investigation of the Nickel-Catalyzed Transfer Hydrocyanation of Alkynes.” <i>ACS Catalysis</i>. American Chemical Society, 2023. <a href=\"https://doi.org/10.1021/acscatal.3c02977\">https://doi.org/10.1021/acscatal.3c02977</a>.","short":"J. Reisenbauer, P. Finkelstein, M.-O. Ebert, B. Morandi, ACS Catalysis 13 (2023) 11548–11555.","ama":"Reisenbauer J, Finkelstein P, Ebert M-O, Morandi B. Mechanistic investigation of the nickel-catalyzed transfer hydrocyanation of alkynes. <i>ACS Catalysis</i>. 2023;13(17):11548-11555. doi:<a href=\"https://doi.org/10.1021/acscatal.3c02977\">10.1021/acscatal.3c02977</a>","ista":"Reisenbauer J, Finkelstein P, Ebert M-O, Morandi B. 2023. Mechanistic investigation of the nickel-catalyzed transfer hydrocyanation of alkynes. ACS Catalysis. 13(17), 11548–11555.","ieee":"J. Reisenbauer, P. Finkelstein, M.-O. Ebert, and B. Morandi, “Mechanistic investigation of the nickel-catalyzed transfer hydrocyanation of alkynes,” <i>ACS Catalysis</i>, vol. 13, no. 17. American Chemical Society, pp. 11548–11555, 2023.","mla":"Reisenbauer, Julia, et al. “Mechanistic Investigation of the Nickel-Catalyzed Transfer Hydrocyanation of Alkynes.” <i>ACS Catalysis</i>, vol. 13, no. 17, American Chemical Society, 2023, pp. 11548–55, doi:<a href=\"https://doi.org/10.1021/acscatal.3c02977\">10.1021/acscatal.3c02977</a>."},"type":"journal_article","date_published":"2023-08-16T00:00:00Z","page":"11548-11555","issue":"17","oa_version":"Published Version","tmp":{"short":"CC BY (4.0)","image":"/images/cc_by.png","legal_code_url":"https://creativecommons.org/licenses/by/4.0/legalcode","name":"Creative Commons Attribution 4.0 International Public License (CC-BY 4.0)"},"year":"2023","OA_place":"publisher","month":"08","author":[{"id":"51d862e9-36ee-11f0-86d3-8534c85a5496","last_name":"Reisenbauer","first_name":"Julia","full_name":"Reisenbauer, Julia"},{"last_name":"Finkelstein","full_name":"Finkelstein, Patrick","first_name":"Patrick"},{"full_name":"Ebert, Marc-Olivier","first_name":"Marc-Olivier","last_name":"Ebert"},{"last_name":"Morandi","first_name":"Bill","full_name":"Morandi, Bill"}],"has_accepted_license":"1","date_updated":"2025-12-16T11:11:14Z","volume":13,"user_id":"2DF688A6-F248-11E8-B48F-1D18A9856A87","day":"16","external_id":{"pmid":["37671177"]},"publication":"ACS Catalysis","publisher":"American Chemical Society","oa":1,"date_created":"2025-12-09T14:23:42Z","doi":"10.1021/acscatal.3c02977","scopus_import":"1","article_type":"original","publication_status":"published","_id":"20760","language":[{"iso":"eng"}],"title":"Mechanistic investigation of the nickel-catalyzed transfer hydrocyanation of alkynes","publication_identifier":{"eissn":["2155-5435"]},"quality_controlled":"1","intvolume":"        13","pmid":1,"PlanS_conform":"1","abstract":[{"text":"The implementation of HCN-free transfer hydrocyanation reactions on laboratory scales has recently been achieved by using HCN donor reagents under nickel- and Lewis acid co-catalysis. More recently, malononitrile-based HCN donor reagents were shown to undergo the C(sp3)–CN bond activation by the nickel catalyst in the absence of Lewis acids. However, there is a lack of detailed mechanistic understanding of the challenging C(sp3)–CN bond cleavage step. In this work, in-depth kinetic and computational studies using alkynes as substrates were used to elucidate the overall reaction mechanism of this transfer hydrocyanation, with a particular focus on the activation of the C(sp3)–CN bond to generate the active H–Ni–CN transfer hydrocyanation catalyst. Comparisons of experimentally and computationally derived 13C kinetic isotope effect data support a direct oxidative addition mechanism of the nickel catalyst into the C(sp3)–CN bond facilitated by the coordination of the second nitrile group to the nickel catalyst.","lang":"eng"}]}