This perspective article, from workers at Imperial College London and Pfizer, Cambridge, reviews the literature on site-selectivity in S-M coupling reactions for a wide variety of heterocycles on a case-by-case basis. It is shown that experimental parameters can critically impact the dominant catalytic species in solution and its ability to undergo the site-selectivity determining oxidative addition step, and hence the ratio of resultant products. Attention to details, as always, important in these reactions. This short review is a must-read for anyone wishing to develop (and possibly scale up) S-M reactions with heterocyclic components.
Almond-Thynne et al Chemical Science, 8, 40-62