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Completely linear: a general and practical palladium-catalyzed linear-selective Negishi coupling of 3,3-disubstituted allylzinc reagents with aryl, heteroaryl and vinyl electrophiles at ambient temperature is described. This method provides an effective means to access a wide range of prenylated arenes or skipped dienes in a completely linear-selective fashion, as demonstrated by a concise synthesis of the anti-HIV natural product siamenol. Finally, DFT calculations shed light on the origin of the excellent regioselectivity observed with the current catalyst system.
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Yang et al. (2013) studied this question.
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