Science of Synthesis

Couladouros, E. A.; Strongilos, A. T., Science of Synthesis, (2006) 28, 295.

Palladium chemistry has been demonstrated to be a very efficient tool for the preparation of naphtho-1,4-quinone derivatives ‌159‌ in high yields. Thus, 2-bromonaphtho-1,4-quinones react with alkyl-, alkenyl-, or arylstannanes in the presence of a suitable palladium catalyst to afford the corresponding coupled product (‌Table 26‌).[‌633‌,‌892‌–‌894‌,‌1016‌,‌1142‌,‌1147‌,‌1148‌] This Stille-type coupling reaction usually takes place with a copper(I) salt as a cocatalyst.[‌1149‌] Quinones may also be transformed into the corresponding stannylquinones and consequently used for a Stille-type coupling reaction.[‌1150‌,‌1151‌] 2-Bromonaphtho-1,4-quinones also undergo Suzuki[‌1152‌,‌1153‌] or Suzuki–Miyaura coupling[‌1015‌] with boronic acid derivatives (‌Scheme 78‌). Coupling reactions of halogenated naphtho-1,4-quinones with terminal alkynes under Sonogashira conditions have been reported.[‌1154‌,‌1155‌]

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M8	M8	M8	M8	M8	Meeeeeeeee	Meeee (%)	Mee
MMe	M	M		Me	Me(MMe8)8, MeM, MMM, 88 °M, 8 e	88	[‌888‌]
MM	M	M	Me	Me	Me(MMe8)8, MeMe, eeeeeee, eeeeee, 88 e	88	[‌8888‌]
MM	M	M		Me	Me(MMe8)8, MeMe, eeeeeee, eeeeee, 8 e	888	[‌8888‌]
M	MMe	MM	Me	Me	Me(MMe8)8, MeMe, eeeeeee, eeeeee, 88 e	888	[‌8888‌]
M	Me	MMe		Me	MeMe8(MMe8)8, eeeeeee, eeeeee, eeeeeeeee	88	[‌8888‌]

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8-Meeeeee-8-(8-eeeeeee-8,8-eeeee-8,8-eeeeeeeeeeeeeeeee-8-ee)-8-eeeeeeeeeeeeeeeeee (‌888‌, M8 = MMe; M8 = M8 = M; M8 = 8-Meeeee-8-eeeeeee-8-eeeeeeeeeeee):[‌888‌]

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References

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• 8.Meeeee-Meee, (8888) 88/8e, 888.