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Please login to access the full content or check if you have access via1.1 Product Class 1: Organometallic Complexes of Nickel
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Montgomery, J., Science of Synthesis, (2001) 1, 11.
General Introduction
This contribution provides an overview of contemporary synthetic methods of broad applicability that involve the preparation and use of nickel π-complexes as starting materials or reactive intermediates. Numerous excellent reviews on the chemistry of nickel have appeared that are complementary to this contribution in subject and scope. An outstanding review by Chetcuti describes the known π-complexes of nickel,[1] and several other structural classes of nickel complexes have been reviewed;[2–4] σ-bonded organonickel compounds are reviewed in Houben–Weyl, Vol. 13/9b, pp 632–700. The historical development and early applications of nickel chemistry have been reviewed by Wilke[5] and Jolly,[6] industrial applications have been reviewed by Keim,[7] and several other reviews on specific groups of synthetic transformations have appeared.[8–12,187] The organometallic chemistry of nickel has a rich history dating back more than 100 years.[5] Despite its long history, fundamentally new reactions are still being developed at a rapid pace. Furthermore, existing reactions are being applied in new and creative ways to solve long-standing challenges in organic synthesis. More and more of the synthetic organic community is beginning to realize that nickel catalysis provides preparatively convenient reactions of broad scope in a variety of contexts. In many cases, the reactivity exhibited by nickel may not be achieved by any other transition element. At this time, organonickel chemistry seems to be well poised to provide an increasing number of new reactions and interesting mechanistic questions, as well as to gain an increasingly important role in the organic chemist's repertoire of mainstream synthetic transformations.
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Mee(η8-eeeeeeeee-8,8-eeeee)eeeeee(8) (8):[88]
M 888-eM Meeeeee eeeee eeeeeeee eeee e eeeeeeee eee eee e eeeeeeee-eeeeeeeeee eeeeeeee eeeeee eee eeeeeee eeee eeeeeeeee eeeee [Me(eeee)8] (8; 8.88 e, 8.8888 eee, 8.88 eeeee) eee eeeeeee eeeee eeeee eeeeee eeee e eeee eee. Meeee eeeeeee eee eeeeeeeeeeee e eeeeeeee M8 eeeeeeeeee, eee eeeee eee eeeeeeeee ee MMM (88 eM) eee eeeeeee eeee eeeeeeeee-8,8-eeeee (8.88 e, 8.8888 eee, 8.88 eeeee). Mee eeeeeeeeee eee eeeeee ee −88 °M eeee e eee eee/eeeeeee eeee ee eeee e eeeee eeeeee. M 8.8 M eeee ee MMMMM-M ee MMM (88.8 eM, 8.8888 eee, 8.88 eeeee) eee eeeeeeeeeee ee eee eeeeeeee eeeeee eeeee M8 eee e eeeeeee. Mee MMMMM-M eeee eee eeeee eeee 8 e ee eeee e eeee, eeeeeee-eeeee eeee eeeee eee eeeeeee ee eeee ee 8 °M eeee e 8 e eeeeee. Mee eeee eee eeeeeee eeee Me8M (88 eM) ee eeee e eeeee eeeeee eeeeeeeeeee. Mee eeeeeeeeee eee eeeeee ee −88 °M eee eeeeeee ee eeeee eee 88 e ee eeeeeeee eeeeeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeee ee −88 °M eee e eeeeee eeeee eeeeee eeeeeee, eeeeee eeee eeee Me8M (88 eM eeeeeeee) eeeee eee eeeee eeeeeeee eeee eeeeeee, eee eeeee ee eeeee. [Me(eee)8] (8) eee eeeeeeee ee e eeee eeeeee eeeeee eee eee eeeeeeee eee eeeeeeeee eee; eeeee: 8.8 e (88%).
Mee eeeeeeee eee ee eeeeeeeeeeeeee ee eee eeeeeeeee eeeeeeeee. Me e eeeeeeee, eeeee [Me(eee)8] (8.8 e) eee eeeeeeeee ee e eeeeeee eeeeee ee eeeeeee (88 eM · e−8) ee 88 °M eee eeeeeee eeeeeeee eeeeeee Meeeee ee eeeeee eeeeeeee eeeeee. Mee eeee eeeeee eeee eee eeeeeee ee eeeee ee −88 °M eee 88 e ee eeee eeeeee eeeeee-eeeeee eeeeeee. Meeeeee ee eee eeeeeeeeeee ee −88 °M eeeeeee e eeeeee eeeee eeeeee eeeeeee, eeeeeeee ee e eeeeeee eeee (8 × 88 eM), eeee eeee eeeeeeee; eeeee: 8.88 e (88%).
Meeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeee(MM) (8):[88]
M eeee ee MeMe8•8M8M (8.88 e, 8.88 eee) ee M8M (8 eM) eee eeeeeee eeee eeeeeee MeMM (88 eM), eee Me8M (8.88 e, 8.88 eee) ee eeeeeee MeMM (88 eM) eee eeeee. Mee eeeee-eeeee eeeeeeeeeeeeeeee eeeeeeeeeee, eeee eeee ee eeeeeee eeee eee eeeeee eeeeee eee 88 e, eeee eeee eeee eeeeeeee eeeee eeee eeeeeeee eee, eeeeee eeee eeeeeee MeMM, eee eeeee ee e eeeeee eeeeeeeeee (M8MM8, MMM); eeeee: 8.88 e (88%).
References
[1] | Meeeeeee, M. M., Me Meeeeeeeeeeee Meeeeeeeeeeeee Meeeeeeee MM, Meee, M. M.; Meeee, M. M. M.; Meeeeeeee, M., Mee.; Meeeeeee: Mee Meee, (8888); Mee. 8, e 888. |
[2] | Meeeee, M. M., Me Meeeeeeeeeeee Meeeeeeeeeeeee Meeeeeeee MM, Meee, M. M.; Meeee, M. M. M.; Meeeeeeee, M., Mee.; Meeeeeee: Mee Meee, (8888); Mee. 8, e 8. |
[3] | Meeee, M. M., Me Meeeeeeeeeeee Meeeeeeeeeeeee Meeeeeeee MM, Meee, M. M.; Meeee, M. M. M.; Meeeeeeee, M., Mee.; Meeeeeee: Mee Meee, (8888); Mee. 8, e 88. |
[4] | Meeee, M. M., Me Meeeeeeeeeeee Meeeeeeeeeeeee Meeeeeeee, Meeeeeeee, M., Me.; Meeeeeee: Meeeee, (8888); Mee. 8, ee 888, 888. |
[5] | Meeee, M., Meeee. Meee., (8888) 888, 888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 888. |
[6] | Meeee, M. M.; Meeee, M., Mee Meeeeee Meeeeeeee ee Meeeee, Meeeeeee: Mee Meee, (8888); Meee.8–8. |
[7] | Meee, M., Meeee. Meee., (8888) 888, 888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 888. |
[8] | Meeeeeeeee, M. M., Mee. Meeee., (8888) 88, 888. |
[9] | Meeeeeeeee, M. M.; Meeeeee, M. M., Meeeeeee ee Meeee-Meeeeee Meeeeeeee, Meeeeeeeee, M. M., Me.; MMM Meeee: Meeeee, (8888); Mee. 8, e 8. |
[10] | Meeeeeee, M. M., Mee. Meee. Mee., (8888) 8, 888. |
[11] | Meeeee, M. M., Me Meeeeeeeeeee ee Meeeeeeee Meeeeeeee, Meee, M. M., Me.; Meeee: Meeeeeeeee, (8888); Mee. 8, e 8888. |
[12] | Meeee, M. M., Me Meeeeeeeeeeee Meeeeeeeeeeeee Meeeeeeee, Meeeeeeee, M., Me.; Meeeeeee: Meeeee, (8888); Mee. 8, ee 888, 888, 888, 888. |
[13] | Meeeee, M. M.; Meeeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[14] | Meeeeee, M. M., M. Meee. Mee., (8888), 888. |
[187] | Máeeeee, M.; Meeee, M.; Meeeeee, M., Meeeeeeeeeee Meeeeeeee Meeeeee, (8888) 888, 888. |
[188] | Meeeeeeee, M. M., Meeeeee ee Meeeeeeeee – Meeeeeee Meeeeeeeee, (8888) 88, 888. |