Suzuki Coupling

The scheme above shows the first published Suzuki Coupling, which is the palladium-catalysed cross coupling between organoboronic acid and halides. Recent catalyst and methods developments have broadened the possible applications enormously, so that the scope of the reaction partners is not restricted to aryls, but includes alkyls, alkenyls and alkynyls. Potassium trifluoroborates and organoboranes or boronate esters may be used in place of boronic acids. Some pseudohalides (for example triflates) may also be used as coupling partners.

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Mechanism of the Suzuki Coupling

One difference between the Suzuki mechanism and that of the Stille Coupling is that the boronic acid must be activated, for example with base. This activation of the boron atom enhances the polarisation of the organic ligand, and facilitates transmetallation. If starting materials are substituted with base labile groups (for example esters), powdered KF effects this activation while leaving base labile groups unaffected.

In part due to the stability, ease of preparation and low toxicity of the boronic acid compounds, there is currently widespread interest in applications of the Suzuki Coupling, with new developments and refinements being reported constantly.

Recent Literature

Alkyl-Alkyl Suzuki Cross-Couplings of Unactivated Secondary Alkyl Halides at Room Temperature
B. Saito, G. C. Fu, J. Am. Chem. Soc., 2007, 129, 9602-9603.

Boronic Acids: New Coupling Partners in Room-Temperature Suzuki Reactions of Alkyl Bromides. Crystallographic Characterization of an Oxidative-Addition Adduct Generated under Remarkably Mild Conditions
J. H. Kirchhoff, M. R. Netherton, I. D. Hill, G. C. Fu, J. Am. Chem. Soc., 2002, 124, 13662-13663.

Suzuki cross-couplings of alkyl bromides that contain β hydrogens run under surprisingly mild conditions (room temperature). This work represents a significant expansion in the scope of the Suzuki reaction.
M. R. Netherton, C. Dai, K. Neuschütz, G. C. Fu, J. Am. Chem. Soc., 2001, 123, 10099-10100.

B-Alkyl sp³-sp² Suzuki-Miyaura Couplings under Mild Aqueous Micellar Conditions
N. R. Lee, R. T. H. Linstadt, D. J. Gloisten, F. Gallou, B. H. Lipshutz, Org. Lett., 2018, 20, 2902-2905.

Rational Exploration of N-Heterocyclic Carbene (NHC) Palladacycle Diversity: A Highly Active and Versatile Precatalyst for Suzuki-Miyaura Coupling Reactions of Deactivated Aryl and Alkyl Substrates
G.-R. Peh, E. A. B. Kantchev, J.-C. Er, J. Y. Ying, Chem. Eur. J., 2010, 14, 4010-4017.

Stereoconvergent Amine-Directed Alkyl-Alkyl Suzuki Reactions of Unactivated Secondary Alkyl Chlorides
Z. Lu, A. Wilsily, G. C. Fu, J. Am. Chem. Soc., 2011, 133, 8154-8157.

A Catalytic Enantiotopic-Group-Selective Suzuki Reaction for the Construction of Chiral Organoboronates
C. Sun, B. Potter, J. P. Morken, J. Am. Chem. Soc., 2014, 136, 6534-6537.

Tetraphosphine/palladium catalysed Suzuki cross-coupling reactions of aryl halides with alkylboronic acids
I. Kondolff, H. Doucet, M. Santelli, Tetrahedron, 2004, 60, 3813-3818.

Suzuki-Miyaura Cross-Coupling Reactions of Primary Alkyltrifluoroborates with Aryl Chlorides
S. D. Dreher, S.-E. Lim, D. L. Sandrock, G. A. Molander, J. Org. Chem., 2009, 74, 3626-3631.

A Concise and Atom-Economical Suzuki-Miyaura Coupling Reaction Using Unactivated Trialkyl- and Triarylboranes with Aryl Halides
H. Li, Y.-L. Zhong, C.-y. Chen, A. E. Ferraro, D. Wang, Org. Lett., 2015, 17, 3616-3619.

[(NHC)PdCl₂(Aniline)] Complexes: Easily Synthesized, Highly Active Pd(II)-NHC Precatalysts for Cross-Coupling Reactions
Q. Xia, S. Shi, P. Gao, R. Lalancette, R. Szostak, M. Szostak, J. Org. Chem., 2021, 86, 15650-15657.

Stereospecific Pd-Catalyzed Cross-Coupling Reactions of Secondary Alkylboron Nucleophiles and Aryl Chlorides
L. Li, S. Zhao, A. Joshi-Pangu, M. Diane, M. R. Biscoe, J. Am. Chem. Soc., 2014, 136, 14027-14030.

Pd(N,N-Dimethyl β-alaninate)₂ as a High-Turnover-Number, Phosphine-Free Catalyst for the Suzuki Reaction
X. Cui, T. Qin, J.-R. Wang, L. Liu, Q.-X. Guo, Synthesis, 2007, 393-399.

Guanidine/Pd(OAc)₂-Catalyzed Room Temperature Suzuki Cross-Coupling Reaction in Aqueous Media under Aerobic Conditions
S. Li, Y. Lin, J. Cao, S. Zhang, J. Org. Chem., 2007, 72, 4067-4072.

Aqueous Suzuki-Miyaura Coupling with Ultralow Palladium Loading and Simple Product Separation
W. Yang, W.-D. Xu, J.-J. Ning, Z.-G. Ren, D. J. Young, Synlett, 2020, 31, 1303-1307.

Pd₂(dba)₃/P(t-Bu)₃ catalyzes Suzuki cross-coupling of arylboronic acids with a wide range of aryl and vinyl halides, including chlorides, typically at room temperature, while the combination of Pd(OAc)₂/PCy₃ is suitable for a diverse array of aryl and vinyl triflates. Together, these two catalyst systems cover a broad spectrum of commonly encountered substrates for Suzuki couplings.
A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc., 2000, 122, 4020-4028.

Liquid-Assisted Grinding Accelerating: Suzuki-Miyaura Reaction of Aryl Chlorides under High-Speed Ball-Milling Conditions
Z.-J. Jiang, Z.-H. Li, J.-B. Yu, W.-K. Su, J. Org. Chem., 2016, 81, 10049-10055.

[Bmim]PF₆-Promoted Ligandless Suzuki-Miyaura Coupling Reaction of Potassium Aryltrifluoroborates in Water
L. Liu, Y. Dong, B. Pang, J. Ma, J. Org. Chem., 2014, 79, 7193-7198.

Sterically Demanding, Water-Soluble Alkylphosphines as Ligands for High Activity Suzuki Coupling of Aryl Bromides in Aqueous Solvents
K. H. Shaughnessy, R. S. Booth, Org. Lett., 2001, 3, 2757-2759.

Convenient and Efficient Suzuki-Miyaura Cross-Coupling Catalyzed by a Palladium/Diazabutadiene System
G. A. Grasa, A. C. Hillier, S. P. Nolan, Org. Lett., 2001, 3, 1077-1080.

An Indefinitely Air-Stable σ-Ni^II Precatalyst for Quantitative Cross-Coupling of Unreactive Aryl Halides and Mesylates with Aryl Neopentylglycolboronates
J. Malineni, R. L. Jezorek, N. Zhang, V. Percec, Synthesis, 2016, 48, 2795-2807.

Copper-Catalyzed Suzuki-Miyaura Coupling of Arylboronate Esters: Transmetalation with (PN)CuF and Identification of Intermediates
S. K. Gurung, S. Thapa, A. Kafle, D. A. Dickie, R. Giri, Org. Lett., 2014, 16, 1264-1267.

The Rational Design and Synthesis of Water-Soluble Thiourea Ligands for Recoverable Pd-Catalyzed Aerobic Aqueous Suzuki-Miyaura Reactions at Room Temperature
W. Chen, X.-Y. Lu, B.-Hua, W.-g. Yu, Z.-n. Zhou, Y. Hu, Synthesis, 2018, 50, 1499-1510.

A Cyclobutene-1,2-Bis(imidazolium) Salt as Efficient Precursor of Palladium-Catalyzed Room-Temperature Suzuki-Miyaura Reactions
A. Rahimi, A. Schmidt, Synlett, 2010, 1327-1330.

An Extremely Active and General Catalyst for Suzuki Coupling Reaction of Unreactive Aryl Chlorides
D.-H. Lee, M.-J. Jin, Org. Lett., 2011, 13, 252-255.

A Triarylphosphine Ligand Bearing Dodeca(ethylene glycol) Chains: Enhanced Efficiency in the Palladium-Catalyzed Suzuki-Miyaura Coupling Reaction
T. Fujihara, S. Yoshida, J. Terao, Y. Tsuji, Org. Lett., 2009, 11, 2121-2124.

A New Family of Tunable Indolylphosphine Ligands by One-Pot Assembly and Their Applications in Suzuki-Miyaura Coupling of Aryl Chlorides
C. M. So, C. C. Yeung, C. P. Lau, F. Y. Kwong, J. Org. Chem., 2008, 73, 7803-7806.

An Active, General, and Long-Lived Palladium Catalyst for Cross-Couplings of Deactivated (Hetero)aryl Chlorides and Bromides with Arylboronic Acids
T. Hoshi, T. Honma, A. Mori, M. Konishi, T. Sato, H. Hagiwara, T. Suzuki, J. Org. Chem., 2013, 78, 11513-11524.

Biphenylene-Substituted Ruthenocenylphosphine for Suzuki-Miyaura Coupling of Aryl Chlorides
T. Hoshi, T. Nakazawa, I. Saitoh, Y. Mori, T. Suzuki, J.-i. Sakai, H. Hagiwara, S. Akai, Org. Lett., 2008, 10, 2063-2066.

Scope of the Two-Step, One-Pot Palladium-Catalyzed Borylation/Suzuki Cross-Coupling Reaction Utilizing Bis-Boronic Acid
G. A. Molander, S. L. J. Trice, S. M. Kennedy, J. Org. Chem., 2012, 77, 8678-8688.

Facile Synthesis of Highly Stable Gold Nanoparticles and Their Unexpected Excellent Catalytic Activity for Suzuki-Miyaura Cross-Coupling Reaction in Water
J. Han, Y. Liu, R. Guo, J. Am. Chem. Soc., 2009, 131, 2060-2061.

Biscarboxy-Functionalized Imidazole and Palladium as Highly Active Catalytic System in Protic Solvents: Methanol and Water
R. Martínez, I. M. Pastor, M. Yus, Synthesis, 2014, 46, 2965-2975.

Room-Temperature Suzuki-Miyaura Couplings in Water Facilitated by Nonionic Amphiphiles
B. H. Lipshutz, T. B. Petersen, A. R. Abela, Org. Lett., 2008, 10, 1333-1336.

Robust Acenaphthoimidazolylidene Palladium Complexes: Highly Efficient Catalysts for Suzuki-Miyaura Couplings with Sterically Hindered Substrates
T. Tu, Z. Sun, W. Fang, M. Xu, Y. Zhou, Org. Lett., 2012, 14, 4250-4253.

Solvent-Free Microwave-Assisted Suzuki-Miyaura Coupling Catalyzed by PEPPSI-iPr
P. Nun, J. Martinez, F. Lamaty, Synlett, 2009, 1761-1764.

Cross-Coupling and Dehalogenation Reactions Catalyzed by (N-Heterocyclic carbene)Pd(allyl)Cl Complexes
O. Navarro, H. Kaur, P. Mahjoor, S. P. Nolan, J. Org. Chem., 2004, 69, 3173-3180.

An N-Heterocyclic Carbene Ligand with Flexible Steric Bulk Allows Suzuki Cross-Coupling of Sterically Hindered Aryl Chlorides at Room Temperature
G. Altenhoff, R. Goddard, C. W. Lehmann, F. Glorius, Angew. Chem. Int. Ed., 2003, 42, 3690-3693.

Ferrocenyl Monophosphine Ligands: Synthesis and Applications in the Suzuki-Miyaura Coupling of Aryl Chlorides
C. Baillie, L. Zhang, J. Xiao, J. Org. Chem., 2004, 69, 7779-7782.

Reusable and Efficient Pd(OAc)₂/TBAB/PEG-400 System for Suzuki-Miyaura Cross-Coupling Reaction under Ligand-Free Conditions
W.-J. Liu, Y.-X. Xie, Y. Liang, J.-H. Li, Synthesis, 2006, 860-864.

Phosphine-Free Palladium Acetate Catalyzed Suzuki Reaction in Water
L. Liu, Y. Zhang, Y. Wang, J. Org. Chem., 2005, 70, 6122-6125.

Cyrene as a Bio-Based Solvent for the Suzuki-Miyaura Cross-Coupling
K. L. Wilson, J. Murray, C. Jamieson, A. J. B. Watson, Synlett, 2018, 29, 650-654.

Synthesis and Characterization of R2PN=P(ⁱBuNCH₂CH₂)₃N: A New Bulky Electron-Rich Phosphine for Efficient Pd-Assisted Suzuki-Miyaura Cross-Coupling Reactions
J. V. Kingston, J. G. Verkade, J. Org. Chem., 2007, 72, 2816-2822.

Modified (NHC)Pd(allyl)Cl (NHC = N-Heterocyclic Carbene) Complexes for Room-Temperature Suzuki-Miyaura and Buchwald-Hartwig Reactions
N. Marion, O. Navarro, J. Mei, E. D. Stevens, N. M. Scott, S. P. Nolan, J. Am. Chem. Soc., 2006, 128, 4101-4111.

Aryl Boronic Esters Are Stable on Silica Gel and Reactive under Suzuki-Miyaura Coupling Conditions
N. Oka, T. Yamada, H. Sajiki, S. Akai, T. Ikawa, Org. Lett., 2022, 24, 3510-3514.

A Highly Active Catalyst for Suzuki-Miyaura Cross-Coupling Reactions of Heteroaryl Compounds
K. L. Billingsley, K. W. Anderson, S. L. Buchwald, Angew. Chem. Int. Ed., 2006, 45, 3484-3488.

Palladium catalyzed Suzuki-Miyaura coupling with aryl chlorides using a bulky phenanthryl N-heterocyclic carbene ligand
C. Song, Y. Ma, Q. Chai, C. Ma, W. Jiang, M. B. Andrus, Tetrahedron, 2005, 61, 7438-7446.

PVC-Supported Palladium Nanoparticles: An Efficient Catalyst for Suzuki Cross-Coupling Reactions at Room Temperature
M. Samarasimhareddy, G. Prabhu, T. M. Vishwanatha, V. V. Sureshbabu, Synthesis, 2013, 45, 1201-1206.

Recyclable Catalysts for Suzuki-Miyaura Cross-Coupling Reactions at Ambient Temperature Based on a Simple Merrifield Resin Supported Phenanthroline-Palladium(II) Complex
J. Yang, P. Li, L. Wang, Synthesis, 2011, 1295-1301.

Immobilization of Dipyridyl Complex to Magnetic Nanoparticle via Click Chemistry as a Recyclable Catalyst for Suzuki Cross-Coupling Reactions
G. Lv, W. Mai, R. Jin, L. Gao, Synlett, 2008, 1418-1422.

PdEDTA Held in an Ionic Liquid Brush as a Highly Efficient and Reusable Catalyst for Suzuki Reactions in Water
J.-F. Wei, J. Jiao, J.-J. Feng, J. Lv, X.-R. Zhang, X.-Y. Shi, Z.-G. Chen, J. Org. Chem., 2009, 74, 5967-5974.

Palladium-Imidazolium Carbene Catalyzed Aryl, Vinyl, and Alkyl Suzuki-Miyaura Cross Coupling
M. B. Andrus, C. Song, Org. Lett., 2001, 3, 3761-3764.

Overcoming the Naphthyl Requirement in Stereospecific Cross-Couplings to Form Quaternary Stereocenters
J. Xu, O. P. Bercher, M. P. Watson, J. Am. Chem. Soc., 2021, 143, 8608-8613.

Vinyl Thianthrenium Tetrafluoroborate: A Practical and Versatile Vinylating Reagent Made from Ethylene
F. Juliá, J. Yan, F. Paulus, T. Ritter, J. Am. Chem. Soc., 2021, 143, 12992-12998.

Ligand Effects on the Stereochemical Outcome of Suzuki-Miyaura Couplings
G.-P. Lu, K. R. Voigtritter, C. Cai, B. H. Lipshutz, J. Org. Chem., 2012, 77, 3700-3703.

Synthesis of E-Alkyl Alkenes from Terminal Alkynes via Ni-Catalyzed Cross-Coupling of Alkyl Halides with B-Alkenyl-9-borabicyclo[3.3.1]nonanes
T. Di Franco, A. Epenoy, X. Hu, Org. Lett., 2015, 17, 4910-4913.

Highly E-Selective, Stereoconvergent Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Alkenyl Ethers
G.-M. Ho, H. Sommer, I. Marek, Org. Lett., 2019, 21, 2913-2917.

MIDA-Vinylsilanes: Selective Cross-Couplings and Applications to the Synthesis of Functionalized Stilbenes
M. G. McLaughlin, C. A. McAdam, M. J. Cook, Org. Lett., 2015, 17, 10-13.

An Efficient and Recyclable Magnetic-Nanoparticle-Supported Palladium Catalyst for the Suzuki Coupling Reactions of Organoboronic Acids with Alkynyl Bromides
X. Zhang, P. Li, Y. Ji, L. Zhang, L. Wang, Synthesis, 2011, 2975-2983.

Efficient Palladium-Catalyzed Cross-Coupling Reaction of Alkynyl Halides with Organoboronic Acids under Aerobic Conditions
J.-S. Tang, M. Tian, W.-B. Sheng, C.-C. Guo, Synthesis, 2012, 44, 541-546.

Suzuki-Miyaura Coupling of Alkynylboronic Esters Generated in Situ from Acetylenic Derivatives
A.-S. Castanet, F. Colobert, T. Schlama, Org. Lett., 2000, 2, 3559-3561.

Highly Active Catalyst for the Heterogeneous Suzuki-Miyaura Reaction: Assembled Complex of Palladium and Non-Cross-Linked Amphiphilic Polymer
Y. M. A. Yamada, K. Takeda, H. Takashashi, S. Ikegami, J. Org. Chem., 2003, 68, 7733-7741.

New Catalysts for Suzuki-Miyaura Coupling Reactions of Heteroatom-Substituted Heteroaryl Chlorides
A. S. Guram, X. Wang, E. E. Bunel, M. M. Faul, R. D. Larsen, M. J. Martinelli, J. Org. Chem., 2007, 72, 5104-5112.

C₂-Symmetric Bis-Hydrazones as Ligands in the Asymmetric Suzuki−Miyaura Cross-Coupling
A. Bermejo, A. Ros, R. Fernández, J. M. Lassaletta, J. Am. Chem. Soc., 2008, 130, 15798-15799.

General Reaction Conditions for the Palladium-Catalyzed Vinylation of Aryl Chlorides with Potassium Alkenyltrifluoroborates
E. Alacid, C. Nájera, J. Org. Chem., 2009, 74, 8191-8195.

Stereoselective Enol Tosylation: Preparation of Trisubstituted α,β-Unsaturated Esters
J. Baxter, D. Steinhuebel, M. Palucki, I. W. Davies, Org. Lett., 2005, 7, 215-218.

N-Vinylpyridinium and -ammonium Tetrafluoroborate Salts: New Electrophilic Coupling Partners for Pd(0)-Catalyzed Suzuki Cross-Coupling Reactions
K. R. Buszek, N. Brown, Org. Lett., 2007, 9, 707-710.

Suzuki-Miyaura Cross-Coupling of Potassium Trifluoroboratohomoenolates
G. A. Molander, D. E. Petrillo, Org. Lett., 2008, 10, 1795-1798.

Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Oxygen-Substituted Allylboronates with Aryl/Vinyl (Pseudo)Halides
J. Li, X. Zhang, Y. Yao, Y. Gao, W. Yang, W. Zhao, J. Org. Chem., 2022, 87, 6951-6959.

Palladium-Catalyzed One-Pot Cross-Coupling of Phenols Using Nonafluorobutanesulfonyl Fluoride
T. Ikawa, K. Saito, S. Akai, Synlett, 2012, 23, 2241-2246.

A family of indolyl phosphine ligands was applied to Suzuki-Miyaura cross-coupling of aryl tosylates with boronic acids, trifluoroborate salts, and boronate esters. Catalyst loading can be reduced to 0.2 mol % for the coupling of nonactivated aryl tosylates.
C. M. So, C. P. Lau, A. S. C. Chan, F. Y. Kwong, J. Org. Chem., 2008, 73, 7731-7734.

A General Palladium Catalyst System for Suzuki-Miyaura Coupling of Potassium Aryltrifluoroborates and Aryl Mesylates
W. K. Chow, C. M. So, C. P. Lau, F. Y. Kwong, J. Org. Chem., 2010, 75, 5109-5112.

Ni(COD)₂/PCy₃ Catalyzed Cross-Coupling of Aryl and Heteroaryl Neopentylglycolboronates with Aryl and Heteroaryl Mesylates and Sulfamates in THF at Room Temperature
P. Leowanawat, N. Zhang, A.-M. Remerita, B. M. Rosen, V. Percec, J. Org. Chem., 2011, 76, 9946-9955.

The First General Palladium Catalyst for the Suzuki-Miyaura and Carbonyl Enolate Coupling of Aryl Arenesulfonates
H. N. Nguyen, X. Huang, S. L. Buchwald, J. Am. Chem. Soc., 2003, 125, 11818-11819.

Synthesis of Biaryl Derivatives via a Magnetic Pd-NPs-Catalyzed One-Pot Diazotization-Cross-Coupling Reaction
Y. Zong, J. Hu, P. Sun, X. Jiang, Synlett, 2012, 23, 2393-2396.

The Suzuki-Miyaura Coupling of Nitroarenes
M. R. Yadav, M. Nagaoka, M. Kashihara, R.-L. Zhong, T. Miyazaki, S. Sakaki, Y. Nakao, J. Am. Chem. Soc., 2017, 139, 9423-9426.

Palladium-Catalyzed Cross-Coupling Reactions of Potassium Alkenyltrifluoroborates with Organic Halides in Aqueous Media
E. Alacid, C. Nájera, J. Org. Chem., 2009, 74, 2321-2327.

The use of bisphosphine ligands with a large P-Pd-P bite angle allowed to synthesize Z-chlorinated internal alkenes in good yields by a selective Suzuki-Miyaura monocoupling process of 9-alkyl-9-BBN with 1,1-dichloro-1-alkenes. These monochlorinated olefins could be further transformed providing stereospecifically trisubstituted olefins.
F. Liron, C. Fosse, A. Pernolet, E. Roulland, J. Org. Chem., 2007, 72, 2220-2223.

Stereoselective Cross-Coupling Reaction of 1,1-Diboryl-1-alkenes with Electrophiles: A Highly Stereocontrolled Approach to 1,1,2-Triaryl-1-alkenes
M. Shimizu, C. Nakamaki, K. Shimono, M. Schelper, T. Kurahashi, T. Hiyama, J. Am. Chem. Soc., 2005, 127, 12506-12507.

Suzuki-Miyaura Cross-Coupling Reactions of Potassium Alkenyltrifluoroborates
G. A. Molander, C. R. Bernardi, J. Org. Chem., 2002, 67, 8424-8429.

Mechanochemical Synthesis of Ketones via Chemoselective Suzuki-Miyaura Cross-Coupling of Acyl Chlorides
J. Zhang, P. Zhang, Y. Ma, M. Szostak, Org. Lett., 2022, 24, 2338-2343.

Suzuki-Miyaura Cross-Coupling of Amides by N-C Cleavage Mediated by Air-Stable, Well-Defined [Pd(NHC)(sulfide)Cl₂] Catalysts: Reaction Development, Scope, and Mechanism
S. Yang, X. Yu, Y. Liu, M. Tomasini, L. Caporaso, A. Poater, L. Cavallo, C. S. J. Cazin, S. P. Nolan, M. Szostak, J. Org. Chem., 2023, 88, 10858-10868.

Evaluation of Cyclic Amides as Activating Groups in N-C Bond Cross-Coupling: Discovery of N-Acyl-δ-valerolactams as Effective Twisted Amide Precursors for Cross-Coupling Reactions
Md. M. Rahman, D. J. Pyle, E. Bisz, B. Dziuk, K. Ejsmont, R. Lalancette, Q. Wang, H. Chen, R. Szostak, M. Szostak, J. Org. Chem., 2021, 86, 10455-10466.

General Method for the Suzuki-Miyaura Cross-Coupling of Primary Amide-Derived Electrophiles Enabled by [Pd(NHC)(cin)Cl] at Room Temperature
P. Lei, G. Meng, Y. Ling, J. An, S. P. Nolan, M. Szostak, Org. Lett., 2017, 19, 6510-6513.

Pd-PEPPSI: Pd-NHC Precatalyst for Suzuki-Miyaura Cross-Coupling Reactions of Amides
P. Lei, G. Meng, Y. Ling, J. An, M. Szostak, J. Org. Chem., 2017, 82, 6638-6646.

Triflamides: Highly Reactive, Electronically Activated N-Sulfonyl Amides in Catalytic N-C(O) Amide Cross-Coupling
S. Shi, R. Lalancette, R. Szostak, M. Szostak, Org. Lett., 2019, 21, 1253-1257.

Sterically Hindered Ketones via Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Amides by N-C(O) Activation
C. Liu, R. Lalancette, R. Szostak, M. Szostak, Org. Lett., 2019, 21, 7976-7981.

Palladium-Catalyzed Suzuki-Miyaura Coupling of Aryl Esters
T. B. Halima, W. Zhang, I. Yalaoui, X. Hong, Y.-F. Yang, K. N. Houk, S. G. Newman, J. Am. Chem. Soc., 2017, 139, 1311-1318.

Palladacycle-Catalyzed Carbonylative Suzuki-Miyaura Coupling with High Turnover Number and Turnover Frequency
P. Gautam, B. M. Bhanage, J. Org. Chem., 2015, 80, 7810-7815.

Carbonylative Suzuki-Miyaura Coupling Reactions of Aryl Iodides with Readily Available Polymer-Immobilized Palladium Nanoparticles
T. Yasukawa, Z. Zhu, Y. Yamashita, S. Kobayashi, Synlett, 2021, 32, 502-504.

Stereospecific Acylative Suzuki-Miyaura Cross-Coupling: General Access to Optically Active α-Aryl Carbonyl Compounds
B. Roh, A. O. Farh, M. Kim, T. Feoktistova, F. Moeller, K. D. Kim, P. H.-Y. Cheong, H. G. Lee, J. Am. Chem. Soc., 2023, 145, 7075-7083.

Deaminative Arylation of Amino Acid-derived Pyridinium Salts
M. E. Hoerrner, K. M. Baker, C. H. Basch, E. M. Bampo, M. P. Watson, Org. Lett., 2019, 21, 7356-7360.

Switchable Selectivity in the Pd-Catalyzed Alkylative Cross-Coupling of Esters
J. Masson-Makdissi, J. K. Vandavasi, S. G. Newman, Org. Lett., 2018, 20, 4094-4098.

Pd/NHC-Catalyzed Enantiospecific and Regioselective Suzuki-Miyaura Arylation of 2-Arylaziridines: Synthesis of Enantioenriched 2-Arylphenethylamine Derivatives
Y. Takeda, Y. Ikeda, A. Kuroda, S. Tanaka, S. Minataka, J. Am. Chem. Soc., 2014, 136, 8544-8547.

Desymmetrization of Vicinal Bis(boronic) Esters by Enantioselective Suzuki-Miyaura Cross-Coupling Reaction
M. Zhang, P. S. Lee, C. Allais, R. A. Singer, J. P. Morken, J. Am. Chem. Soc., 2023, 145, 8308-8313.