定义Definition
铃木偶联反应是钯催化下，有机硼化合物（硼酸或硼酸酯）与有机卤化物或拟卤化物（三氟甲磺酸酯）在碱存在下形成新的 C–C 键的交叉偶联反应，最常用于合成联芳烃。
The Suzuki reaction is a palladium-catalysed cross-coupling of an organoboron compound (boronic acid or ester) with an organic halide or pseudohalide (triflate) in the presence of base to form a C–C bond, most often to make biaryls.
催化循环Catalytic cycle
①Pd(0) 对 R–X 氧化加成得 R–Pd(II)–X；②碱活化硼试剂（形成硼酸盐或 Pd–OH 中间体）后发生转金属化，把 R′ 从硼转移到钯；③还原消除生成 R–R′ 并再生 Pd(0)。
(1) Pd(0) oxidatively adds R–X to give R–Pd(II)–X; (2) after base activates the boron reagent (as a boronate or via Pd–OH), transmetalation moves R′ from boron to palladium; (3) reductive elimination releases R–R′ and regenerates Pd(0).
由来Origin
铃木章与宫浦宪夫于 1979 年报道。铃木章因此与赫克、根岸英一共获 2010 年诺贝尔化学奖（钯催化交叉偶联）。
Reported by Akira Suzuki and Norio Miyaura in 1979; Suzuki shared the 2010 Nobel Prize in Chemistry with Heck and Negishi for palladium-catalysed cross-coupling.
优点与应用Advantages and uses
硼酸稳定、低毒、易得，对水和空气不敏感，副产物硼酸盐易除去，官能团兼容性极好。广泛用于药物（如氯沙坦）、液晶、OLED 材料的合成。大位阻、富电子膦配体（如 SPhos）可活化芳基氯。
Boronic acids are stable, low-toxicity and easy to handle, tolerating water and air; borate by-products are easily removed and functional-group tolerance is excellent. It is used for drugs (e.g. losartan), liquid crystals and OLED materials; bulky electron-rich phosphines (e.g. SPhos) activate aryl chlorides.
反应Reactions
Pd(PPh₃)₄ 或 Pd(OAc)₂/膦配体，K₂CO₃ 等碱，甲苯/水、二氧六环/水，60–100 °C
Pd(PPh₃)₄ or Pd(OAc)₂ with phosphines, K₂CO₃ or similar base, toluene/water or dioxane/water, 60–100 °C
Pd(0) 对卤代芳烃氧化加成。
Oxidative addition of the aryl halide to Pd(0).
碱活化的硼试剂转金属化。
Transmetalation from the base-activated boron reagent.
还原消除生成 C–C 键，再生 Pd(0)。
Reductive elimination forms the C–C bond and regenerates Pd(0).
典型联芳烃合成。
A typical biaryl synthesis.
年表Timeline
- 1979
铃木与宫浦报道该反应
Suzuki and Miyaura report the reaction
- 1981
扩展到芳基硼酸合成联芳烃
Extended to arylboronic acids for biaryls
- 2010
铃木章共获诺贝尔化学奖
Suzuki shares the Nobel Prize in Chemistry