施蒂勒偶联反应Stille reaction

经氧化加成、转金属化（锡到钯）、还原消除的标准循环。有机锡试剂对空气、水稳定，几乎不与羰基等官能团反应，且无需加碱，因此在复杂天然产物合成中很有价值。LiCl、CuI 添加剂可加速转金属化。

It follows oxidative addition, Sn-to-Pd transmetalation and reductive elimination. Stannanes are air- and water-stable, inert toward carbonyls and need no base, making the reaction valuable in complex natural-product synthesis. LiCl or CuI additives speed transmetalation.

小杉正纪、右田俊彦等于 1977 年首先报道有机锡的钯催化偶联；美国化学家约翰·施蒂勒自 1978 年起系统发展，使之成为通用方法。

Kosugi, Migita and co-workers first reported Pd-catalysed coupling of stannanes in 1977; the American chemist John Stille developed it systematically from 1978 into a general method.

有机锡化合物毒性大，锡残留难以从产物中除尽，限制了它在药物生产中的应用，许多场合已被铃木偶联取代。

Organotin compounds are toxic and tin residues are hard to remove, limiting pharmaceutical use; the Suzuki coupling has replaced it in many cases.