Insider dealing: A wide range of polyfunctional (hetero)aromatic and aliphatic zinc reagents can be easily prepared in THF. The compounds are formed by a Zn insertion reaction mediated by the addition of LiCl (see scheme; All=allyl).

The preparation of highly functionalized organometallic compounds can be achieved by direct C-H activation of a broad range of unsaturated substrates using lithium chloride solubilized 2,2,6,6-tetramethylpiperidide bases (TMP(n)MX(m)⋅p LiCl). These are excellent reagents for converting a wide range of aromatic and heterocyclic substrates into valuable organometallic reagents with broad applications in organic synthesis.

In situ generated aryl, heteroaryl, alkyl, or benzylic polyfunctional zinc reagents obtained by the addition of zinc and LiCl to the corresponding organic iodides undergo smooth Pd(0)-catalyzed cross-coupling reactions with aryl bromides, chlorides, and triflates in the presence of PEPPSI as a catalyst. This procedure avoids the manipulation of water and air-sensitive organozinc reagents and produces cross-coupling products in high yields.

Eine Menge Verbindungen: Ein breites Spektrum an funktionalisierten (hetero)aromatischen und aliphatischen Zinkreagentien kann problemlos in Tetrahydrofuran hergestellt werden. Zur Anwendung kommt dabei eine durch Lithiumchlorid vermittelte Zinkinsertion (siehe Schema; All=Allyl).

Efficient Synthesis of Functionalized Organozinc Compounds by the Direct Insertion of Zinc into Organic Iodides and Bromides. -A wide variety of functionalized aryl-, heteroaryl-, and alkylzinc compounds are prepared by treatment of the corresponding iodides or bromides with activated zinc and LiCl in THF. The resulting organozinc compounds are efficiently quenched with electrophiles, in most cases under Cu(I) or Pd(0) catalysis, to give the coupling products in good to excellent yields. -(KRASOVSKIY, A.; MALAKHOV, V.; GAVRYUSHIN, A.; KNOCHEL*, P.; Angew. Chem., Int. Ed. 45 (2006) 36, 6040-6044; Fachbereich Chem. Biochem.,