Science of Synthesis

Elie, M.; Renaud, J.-L.; Gaillard, S., Science of Synthesis: N-Heterocyclic Carbenes in Catalytic Organic Synthesis, (2016) 1, 214.

In 2010, Wu and co-workers reported the intramolecular arylation of benzylic C(sp3)—H bonds catalyzed by an in situ generated palladium–NHC complex, which thus opened access to functionalized fluorenes (‌Scheme 17‌).[‌36‌] In these reactions, the formation of fluorenes appears to be favored over the formation of 9,10-dihydroanthracenes. Thus, 1-bromo-2-(2-tolylmethyl)benzene furnishes 1-methylfluorene through C(sp2)—H bond functionalization rather than 9,10-dihydroanthracene.

‌Meeeee 88‌ Meeeeeeee–MMM Meeeeeeee Meeeeeeee ee Meeeeeeee eeeeeee M(ee8)—M Meee Meeeeeeee ee M(ee8)—M Meee Meeeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

e Meeeeeee eee eeeeeeeee ee 888 °M eee 88 e.

e Meeeeeee eeee eee 8 e.

e Meeeeeee eeee eee 8 e.

Me 8888, Meee eee ee-eeeeeee eeeeeeee eee eeeeeeeee ee eeeeeeeee eeee eeee eeeeeeeee eeeeeeeee ee eeee-eeeeeee eeeeeeeee eeeeeee ‌88‌ ee eeee 8-eeeeeeeeeee eeeeeeeee ‌88‌ (‌Meeeee 88‌).[‌88‌] Me eeeeeeeee eeeeeeeeee eee eee α-eeeeeeeee ee eeeeee (eee Meeeeee ‌8.8.8.8‌), eeeeeee eeeeeeeee ee eee eeeeeeee eeeeeeee ee eeee eeeeeeee ee eeeeeeee eeeee eee ee eeee eeeeeeeeeee eee ee eeeeeeeeee eee eeee eeeee eeeeeeeeee ee eee eeeeeeeee ee eeee 8-eeee-8-eeeeeeeeeeeeeeee ‌88‌. Mee eeeeeeeeeee eeeeeee ee eeee eeeeeeeeeeeeee eeee ee ee eeeeeee eee: Meeeeee, eeeeeeeeeeeeeee eee eeeeeeeee ee eeee eeeeeeee; eee eeeeeeee, ee eee(eeeeeeee) eeeeeeeee eee eeeeeeee, eeee ee eee eeeeee ee eee eeee eeeeeeee ee eeeeeee. Meeeeeeee ee eee eeeeeeeee ee 8,8-eeeeeeeeeeeee eeeeeeeee eee eeee eeee eeeeeeee eeeeeee e eee-eeee (M—M eeee eeeeeeeee/eeeeeeeeee), eee-eee eeeeeeeee.

‌Meeeee 88‌ Meeeeeeee–MMM Meeeeeeee Meeeeeeee ee Meeeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

‌Meeeeeeeeee 88M‌

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeee Meeeeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

Meeee e M8 eeeeeeeeee, e Meeeeee eeee eee eeeeeeeeeeee eeeeeee eeee eee eeeeeeee (8.8 eeee), Me eeeeeee ‌88‌ (8.88 eeee), MMe-Me (8.888 eeee), eeeeeee (8.8 eM), eee eee eeee eeeeeeee (8.88 eeee). Mee eeeeeee eee eeeeeee eeeeeeeeee ee 888 °M eee 88 e, eee ee eee eeee eeeeee ee ee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee ee eeeeeeeee eeeee/MeMMe 88:8 eee eeeeeeee eeeeeee eeee 8-eeeeee-M,M-eeeeeeeeeeeeeee).

References