Science of Synthesis

Eichman, C. C.; Stambuli, J. P., Science of Synthesis: Cross Coupling and Heck-Type Reactions, (2013) 2, 366.

Primary alcohols efficiently undergo cross coupling with aryl halides to form alkyl aryl ethers. The ligands that combine with palladium salts to form active catalysts, ‌4‌,[‌11‌] ‌8‌,[‌12‌] ‌14‌,[‌11‌,‌13‌] ‌15‌,[‌12‌] ‌16‌,[‌12‌] ‌17‌,[‌10‌] and ‌18‌,[‌14‌] are shown in ‌Scheme 4‌. The general scope of the reaction was initially limited due to the β-hydrogen on the alcohol substrate, which resulted in low yields. However, the recent palladium catalyst containing ligand ‌18‌ provides a broad scope that allows both aryl bromides and aryl chlorides to couple with a variety of primary alcohols to give ethers ‌19‌ (‌Table 1‌).[‌14‌]

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