Advanced Organic Chemistry: Organonickel Catalysis

In this installment of the Synthesis Workshop Advanced Organic Chemistry course, Dr. Mark Campbell (Molander lab PhD, Janssen Scientist) joins us to talk about organonickel catalysis as part of our Transition Metal Catalysis module.
This episode also has an associated problem set available at synthesis-workshop.com/#probl....
References (in order of appearance):
Jamison et al. Nature 2014, 509, 299-311; Landrum et al. J. Med. Chem. 2016, 59, 4385-4402; Sabatier, P. Catalysis in Organic Chemistry, D. Van Nostrand Company, NY, 1922, p. 15.
Tamaru, Y. (ed.) Modern Organonickel Chemistry (Wiley-VCH, 2005).
Frenking et al. Organometallics, 2003, 22, 2758-2765.
Chemistry by Rice University is licensed under a Creative Commons Attribution 4.0 International License
Martin et al. ACS Cent. Sci. 2018, 4, 153-165.
Beromi et al. Nat. Rev. Chem. 2017, 1, 0025.
Wang et al. J. Org. Chem. 2014, 79, 4285-4292.
Jarov et al. J. Am. Chem. Soc. 2011, 133, 389-391; Jarvo et al. J. Am. Chem. Soc. 2013, 135, 3303-3306; Watson et al. J. Am. Chem. Soc. 2013, 135, 3307-3310; Doyle et al. Nat. J. Am. Chem. Soc. 2012, 135, 9541-9544; Doyle et al. J. Am. Chem. Soc. 2013, 135, 13605-13609.
Doyle et al. Angew. Chem. Int. Ed. 2011, 50, 6056-6059.
Weix et al. Nature, 2015, 524, 454-457; Weix et al. J. Am. Chem. Soc. 2019, 141, 10978-10983.
Molander et al. J. Am. Chem. Soc. 2008, 130, 9257-9259.
Kambe et al. J. Am. Chem. Soc. 2002, 124, 4222-4223.
Guo et al. Organometallics 2004, 23, 2114-2123.
Fu et al. J. Am. Chem. Soc. 2003, 125, 14726-14727.
Holl et al. Tetrahedron Letters, 1989, 6, 689-692; Madan et. al. J. Org. Chem. 1995, 60, 6574-6581; Montgomery et al. J. Am. Chem. Soc. 2003, 125, 11210-11211 .
Guan et al. Chem. Rev. 2016, 116, 8373-8426; Tamaru, Y. (ed.) Modern Organonickel Chemistry (Wiley-VCH, 2005); He et al. Angew. Chem. Int. Ed. 2015, 54, 4512-4516.
Martin et al. ACS Cent. Sci. 2018, 4, 153-165 ; Yin et al. Angew. Chem. Int. Ed. 2019, 58, 4612-4616
Knochel et al. Tet Lett. 1993, 34, 79111-7914; Knochel et al. Chem. Eur. J. 1996, 2, 1204-1220.
Weix et al. J. Am. Chem. Soc. 2009, 132, 920-921; Weix et al. J. Am. Chem. Soc. 2013, 135, 16192-16197; Diao et al. Synlett. 2021, 32, 1606-1620; Reuping et al. Angew. Chem. Int. Ed. 2020, 59, 6513-6519.
MacMillan et al. 2022, Chem Rev. 122, 1485-1542.
Gutierrez et al. J. Am. Chem. Soc. 2020, 142, 7225-7234.
Doyle et al. J. Am. Chem. Soc. 2016, 138, 12719-12722.
List for further reading:
Tamaru, Y. (ed.) Modern Organonickel Chemistry (Wiley-VCH, 2005)
Ogoshi, S. (ed.) Nickel Catalysis in Organic Synthesis: Methods and Reactions (Wiley-VCH, 2020)
Corream A. (ed.) Ni- and Fe- Based Cross Coupling Reactions (Springer, 2017)
Jamison et al. Nature 2014, 509, 299-311
Ananikov, ACS Catal. 2015, 5, 1964-1971
Diao et al. Acc. Chem. Res. 2020, 53, 906-919
Rueping et al. Chem Sci. 2020, 11, 4051-4064
Weix et al. Acc. Chem. Res. 2015, 48, 1767-1775
Guan et al. Chem. Rev. 2016, 116, 8373-8426
Beromi et al. Nature Reviews, 2017, 1, #0025
Hu et al. Chem. Sci. 2011, 2, 1867-1886
Attributions for paintings on Ni vs Pd slide:
Gustave Doré, Public domain, via Wikimedia Commons
Tommaso Conca, Public domain, via Wikimedia Commons
Attribution for periodic table image: Periodic Table from New York State Education Department: www.nysed.gov/state-assessmen...
Attribution for image of tree: Ping an Chang, CC BY-SA 4.0 creativecommons.org/licenses/..., via Wikimedia Commons

[@arefshaikh5148]

This talk was incredibly informative! I appreciate how well-presented and engaging the content was. Looking forward to more

[@K0wface]

Absolutely agree! This presentation was great and I'll be watching it again and taking notes next time. I'm excited to watch the other episodes too!

[@ganeshkadam8508]

Very Informative talk..

[@calumpatel4956]

Excellent talk! Thank you

[@PlexusTen]

Excellent!

[@m4sterbr0s]

There's an error at 25:55 with the catalytic cycle. After the reductive elimination it should be a Ni(II)-X species, not a Ni(I)-X.

[@UniCorneliusfan21]

we're replacing Pd with this one 🔥