Improve Research Reproducibility A Bio-protocol resource
Concise Method
tooltip

Synthesis of nickel(0) complex 8

BL Braulio M. Puerta Lombardi
MF Morgan R. Faas
DW Daniel West
RS Roope A. Suvinen
HT Heikki M. Tuononen
RR Roland Roesler
request Request a Protocol
ask Ask a question
Favorite

In an argon glovebox, a 25 mL round bottom flask containing a stir bar was charged with 7 (0.355 g, 0.443 mmol) and KC8 (0.180 g, 1.33 mmol). The mixture was attached to a swivel frit and transferred to the vacuum line where it was cooled to −78 °C. THF (15 mL) was subsequently vacuum transferred on top of the solids and the mixture was allowed to warm up to room temperature over 30 minutes. The dark magenta solution was then stirred at room temperature for an additional 30 min, after which the volatiles were removed in vacuo. The residue was extracted with pentane (5 × 10 mL), the solution was filtered, and the solvent was removed in vacuo to yield 8 (0.186 g, 0.290 mmol, 65%) as a microcrystalline black powder. X-ray quality crystals of 8 were obtained via slow evaporation of a pentane solution. Anal. Calcd. for C41H62N2Ni: C 76.75; H 9.74; N 4.37. Found: C 76.59; H 9.69; N 4.34. 1H NMR (THF-d8, 25 °C, 400 MHz): δ 0.95 (d, 3JHH = 6.7 Hz, 3H, CH(CH3)2) 1.09 (d, 3JHH = 6.8 Hz, 3H, CH(CH3)2), 1.10 (s, 3H, CH3), 1.14 (s, 3H, C(CH3)2), 1.23 (s, 3H, C(CH3)2), 1.26 (d, 3JHH = 6.8 Hz, 3H, CH(CH3)2), 1.72 (d, 3JHH = 6.8 Hz, 3H, CH(CH3)2), 1.87 (s, 2H CH2), 2.91 (sept, 3JHH = 6.8 Hz, 1H, CH(CH3)2), 3.16 (sept, 3JHH = 6.7 Hz, 1H, CH(CH3)2), 6.90 (dd, 3JHH = 7.5 Hz, 3JHH = 1.4 Hz, 1H, m-C6H3), 7.00 (dd, 3JHH = 7.5 Hz, 3JHH = 1.4 Hz, 1H, m-C6H3)7.39 (vt, J = 7.5 Hz, 1H, p-C6H3). The highly fluxional signals of the propyl linker were resolved at low temperature. 1H NMR (THF-d8, −88 °C, 400 MHz): δ 1.44 (m, 1H, CCH2CH2), 1.62 (m, 2H, CCH2CH2), 2.07 (m, 1H, CCH2CH2), 2.94 (m, 1H, CCH2CH2), 3.33 (m, 1H, CCH2CH2). 13C NMR (THF-d8, −88 °C, 101 MHz): δ 20.7 (s, CCH2CH2), 22.7, 22.8, 22.9, 23.7, 25.9, 26.0, 26.7, 27.6, 28.3, 28.7 (s, CH(CH3)2), 28.8, 28.9, 29.3 (s, CH(CH3)2), 30.1 (s, CH(CH3)2), 30.4 (s, CH(CH3)2), 30.5, 45.7 (s, CCH2CH2), 47.2 (s, CH2), 54.8 (s, CH2), 60.2 (s, C(CH3)CH2), 60.6 (s, C(CH3)CH2), 68.2, 74.6 (s, C(CH3)2), 75.7 (s, C(CH3)2), 124.0 (s, m-C6H3), 124.3 (s, m-C6H3), 124.5 (s, m-C6H3), 124.5 (s, m-C6H3), 127.6 (s, p-C6H3), 128.1 (s, p-C6H3), 138.6 (s, i-C6H3), 139.0 (s, i-C6H3), 145.1 (s, o-C6H3), 145.6 (s, o-C6H3), 145.7 (s, o-C6H3), 146.1 (s, o-C6H3), 227.2 (s, Ccarbene), 234.4 (s, Ccarbene).

Copyright and License information: The Author(s) ©2024
Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.

Do you have any questions about this protocol?

Post your question to gather feedback from the community. We will also invite the authors of this article to respond.

post Post a Question
0 Q&A