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钯催化下利用烯丙基化合物（如乙酸烯丙酯和烯丙基溴）对亲核试剂（如活性亚甲基化合物，烯醇化合物，胺和酚）进行烯丙基化的反应。
反应机理 Pd(0)-催化剂对双键进行配位得到 η2 π-烯丙基络合物。然后氧化加成，在此过程中离去基团离去，得到 η3 π-烯丙基络合物。此过程也被称为离子化过程： 
根据亲核试剂的强度，此反应可能经过两种不同反应历程。弱亲核试剂（Soft nucleophiles，其共轭酸的pKa < 25）直接加成到烯丙基片段上。而强亲核试剂（ard nucleophiles）首先进攻金属中心，接着还原消除得到烯丙基化合物： 
这两种反应机理模型对于不对称的Tsuji-Trost 反应有至关重要的影响。对于这方面的讨论，可以参阅 Trost 和 Vranken 的研究 (Chem. Rev., 1996, 96, 395. DOI)。 不对称的烯丙基底物一般在位阻较小的一侧进行取代，空间选择性也和亲核试剂的大小有关：
空间位阻较小的亲核试剂（如苯酚）得到空间上更加拥挤的产物。 与此反应类似的反应常用到钼或铱类催化剂。这些反应与Tsuji-Trost反应相同，常常得到空间上更拥挤的异构体： A. Leitner, C. Shu, J. F. Hartwig, Org. Lett., 2005, 7, 1093-1096. 最新文献 
Direct Catalytic Intermolecular α-Allylic Alkylation of Aldehydes by Combination of Transition-Metal and Organocatalysis
I. Ibrahem, A. Córdova, Angew. Chem. Int. Ed., 2006, 45, 1952-1956. 
A Pd(0)-Catalyzed Direct Dehydrative Coupling of Terminal Alkynes with Allylic Alcohols To Access 1,4-Enynes
Y.-X. Li, Q.-Q. Xuan, L. Liu, D. Wang, Y.-J. Chen, C.-J. Li, J. Am. Chem. Soc., 2013, 135, 12536-12539.
A room temperature Pd-catalyzed allylic substitution of a wide range of soft nucleophiles derived from diarylmethane provides rapid access to the corresponding allylated products. A procedure for Pd-catalyzed allylic substitutions to afford diallylation products with quaternary centers is also described.
S.-C. Sha, J. Zhang, P. J. Carroll, P. J. Walsh, J. Am. Chem. Soc., 2013, 135, 17602-17609.
Catalytic Enone Cycloallylation via Concomitant Activation of Latent Nucleophilic and Electrophilic Partners: Merging Organic and Transition Metal Catalysis
B. G. Jellerich, J.-R. Kong, M. J. Krische, J. Am. Chem. Soc., 2003, 125, 7758-7759.
A series of trialkylsilylated chiral aminophosphine ligands are prepared from (S)-prolinol and applied to a palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate with a dimethyl malonate-BSA-LiOAc system.
Y. Tanaka, T. Mino, K. Akita, M. Sakamoto, T. Fujita, J. Org. Chem., 2004, 69, 6679-6687.
Deracemization of Quaternary Stereocenters by Pd-Catalyzed Enantioconvergent Decarboxylative Allylation of Racemic β-Ketoesters
J. T. Mohr, D. C. Behenna, A. M. Harned, B. M. Stoltz, Angew. Chem. Int. Ed., 2005, 44, 6924-6927.
Development of (Trimethylsilyl)ethyl Ester Protected Enolates and Applications in Palladium-Catalyzed Enantioselective Allylic Alkylation: Intermolecular Cross-Coupling of Functionalized Electrophiles
C. M. Reeves, D. C. Behenna, B. M. Stotz, Org. Lett., 2014, 16, 2314-2317.
P-Chirogenic Diaminophosphine Oxide: A New Class of Chiral Phosphorus Ligands for Asymmetric Catalysis
T. Nemoto, T. Matsumoto, T. Masuda, T. Hitomi, K. Hatano, Y. Hamada, J. Am. Chem. Soc., 2004, 126, 3690-3691.
Easy Access to Esters with a Benzylic Quaternary Carbon Center from Diallyl Malonates by Palladium-Catalyzed Decarboxylative Allylation
D. Imao, A. Itoi, A. Yamazaki, M. Shirakura, R. Ohtoshi, K. Ogata, Y. Ohmori, T. Ohta, Y. Ito, J. Org. Chem., 2007, 72, 1534-1537.
Palladium Nanoparticle-Catalyzed C-N Bond Formation. A Highly Regio- and Stereoselective Allylic Amination by Allyl Acetates
L. Adak, K. Chattopadhyay, B. C. Ranu, J. Org. Chem., 2009, 74, 3982-3985.
Allylic Aminations with Hindered Secondary Amine Nucleophiles Catalyzed by Heterobimetallic Pd-Ti Complexes
W. K. Walker, D. L. Anderson, R. W. Stokes, S. J. Smith, D. J. Michaelis, Org. Lett., 2015, 17, 752-755.
Water Enables Direct Use of Allyl Alcohol for Tsuji-Trost Reaction without Activators
H. Kinoshita, H. Shinokubo, K. Oshima, Org. Lett., 2004, 6, 4085-4088.
1-Phosphino-2-sulfenylferrocenes as Planar Chiral Ligands in Enantioselective Palladium-Catalyzed Allylic Substitutions
O. G. Mancheno, J. Priego, S. Cabrera, R. G. Arrayas, T. Llamas, J. C. Carretero, J. Org. Chem., 2003, 68, 3679-3686.
Asymmetric Claisen Rearrangements Enabled by Catalytic Asymmetric Di(allyl) Ether Synthesis
S. G. Nelson, K. Wang, J. Am. Chem. Soc., 2006, 128, 4232-4233.
Catalytic α-Allylation of Unprotected Amino Acid Esters
P. Fang, M. R. Chaulagian, Z. D. Aron, Org. Lett., 2012, 14, 2130-2133.
Palladium-Triethylborane-Triggered Direct and Regioselective Conversion of Allylic Alcohols to Allyl Phenyl Sulfones
S. Chandrasekhar, V. Jagadeshwar, B. Saritha, C. Narsihmulu, J. Org. Chem., 2005, 70, 6506-6507.
Palladium-Catalyzed Dehydrative Allylation of Hypophosphorous Acid with Allylic Alcohols
K. Bravo-Altamirano, J.-L. Montchamp, Org. Lett., 2006,8, 4169-4171.
编译自：Organic Chemistry Portal
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