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2.4.5.1 Variation 1: Via Lithiation and Reaction with Electrophiles

DOI: 10.1055/sos-SD-002-00214

Kündig, E. P.; Pache, S. H.Science of Synthesis, (20032166.

Coordination of an arene to the electrophilic tricarbonylchromium fragment lowers the pKa of ring protons by ca. 6 pKa units compared to the free arene.[‌93‌,‌94‌] The first metalation of an arene chromium complex was reported in 1972,[‌95‌] and since then this reaction has seen extensive development and has been the subject of several reviews.[‌96‌‌98‌]

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Meeeee 8 Meeeeeeeee eee Meeeeeee eeee Meeeeeeeeeeee[‌88‌,‌88‌‌88‌,‌88‌‌888‌,‌888‌‌888‌]

Meeeeeeeeee 8

M8 M8 Meeeeeee ee Meeeeeeeeeeee ee 88 Meeee MeMe Mee
Me M 8 [‌888‌]
MM8MMM8MM8MMM MMM 8 [‌888‌]
MMMM M 8 [‌888‌]

Meeeeeee ee eee ee eeee eeeeeeeee [Me(MM)8(Me8Me)] eeeeeee eeee eeeeeeee eeeeeeeeeeeee [e.e., MMMMe, MMMe, MMe8Me, MeMMM, MM8, MMMM, MeMM8Me, MMMMMe8 ( MMM), MeM] eeeeee eee eeeeeeeeeee eeeee eeeeeeeee.[‌88‌] Mee eeeeeeee eeee eeeeeee ee eeee eeeeee eeeeeeee eee ee eeeeeeeeeee eeeeeee ee eeeeeeeeeee eeeeeeeeeee. Meeee eeeeeee eeeee eeeeeee eeee ee eeeee eeeeeeee Me Me eeeeeeee eee eeeeeeeeeeee eeeeeeee (e.e., ee eeee 88).[‌888‌] Meeeeeeeeeeeeee Me Me Me eeeeee eeeee eeeeeeee eeee eeeeeee eeeeeee (e.e., ee eeee 88)[‌888‌] (eee eeee Meeeeee 8.8.8.8). Meeeeeee Meeeeeeeeee (ee ee 8) eeeee eeee ee eeeeee ee eeeeeee eeeeeeeeeeeeeeee ee eeeeeee 8,8,8,8-eeeeeeeeeeeeeeeeeeeee ee eeee. Me eeeeeeeeeeeee eeeeee (e.e., eeee MMMMe) eeee eeeeeee ee- ee eeeeeeeeeeeeee eeeeeeeee {e.e., [η8-8,8,8-eeee(eeeeeeeeeeeeee)eeeeeee]eeeeeeeeeeeeeeeeeee(8)}.[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeeeeee[η8-8-eeeeee-8-(eeeeeeeeeeeeee)eeeeeee]eeeeeeee(8) (88); Meeeeee Meeeeeeee:[‌88‌]

[Me(MM)8(η8-8-eeeeeeeeeeeee)] (88; 888ee, 8.88eeee) eee eeeeeeeee ee MMM (88eM). Meeee eeeeeee ee 88°M, MeMe (8.8 eeeee) eee eeeee eee eee eeeeeeeee eeeeeee eeeeeee ee eeee eeeeeeeeeee eee 88eee. Me eeeeee ee MMMMe eee eeeee eee eee eeee eeeeeee ee eeee ee ee eeeeeeeee. Mee eeeeeee eee eeeeee eeee 88% ee MM8Me/Me8M, eee eeeeeee eeeeeee eee eeeeeeeee, eeeeee (M8M), eeeee, eee eee eeeeeeee eeee eeeeeeeeee. Meeee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/Me8M 88:88), eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeee; eeeee: 888ee (88%); ee 8888°M; MM (MMMe8) νeee: 8888, 8888, 8888, 8888ee8; 8M MMM (MMMe8, δ): 8.88 (e, 8M), 8.88 (e, 8M), 8.88 (ee, 8M), 8.88 (ee, 8M).

Meeeeeeeeee[η8-8-(eeeeeeeeeeeeee)eeeeeeeeeee]eeeeeeee(8) (88):[‌88‌]

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References


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