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10.6.4.2.2 Of Metals

DOI: 10.1055/sos-SD-010-00275

Andrews, M. D.Science of Synthesis, (200110254.

Dibenzothien-4-yllithium (149) is readily converted into the tin reagent 160 by reaction with tributyltin chloride[‌122‌] or to the boronic acid 161 by quenching with trimethyl borate[‌179‌] (see Volumes 5 and 6, respectively). These reagents are particularly useful for the synthesis of substituted dibenzothiophenes by cross-coupling reactions. For example, reaction of the stannane 160 with the alkene 162 in the presence of a copper complex gives the 4-vinyldibenzothiophene 163 in 71% yield (Scheme 52).[‌180‌] The replacement of lithium with other groups is discussed more fully in Section 10.6.4.2.1.1.

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