Cross-coupling partner

In cross-coupling reactions, the component reagents are called cross-coupling partners or simply coupling partners. These reagents can be further classified according to their nucleophilic vs electrophilic character:

R-X + R'-Y → R-R' + XY

Typically the electrophilic coupling partner (R-X) is an aryl halide, but triflates are also used. Nucleophilic coupling (R'-Y) partners are more diverse. In the Suzuki reaction, boronic esters and boronic acids serve as nucleophilic coupling partners.^[1] Expanding the scope of coupling partners is a focus methods development in organic synthesis.^[2]^[3]

References

^ Kirchhoff, Jan H.; Netherton, Matthew R.; Hills, Ivory D.; Fu, Gregory C. (2002). "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". Journal of the American Chemical Society. 124 (46): 13662–13663. doi:10.1021/ja0283899. PMID 12431081.
^ Denmark, Scott E.; Hung-Chang Liu, Jack (2011). "Discussion Addendum for: Palladium Catalyzed Cross-Coupling of (Z)-1-Heptenyldimethylsilanol with 4-Iodoanisole: (Z)-(1-Heptenyl)-4-methoxybenzene". Organic Syntheses. 88: 102. doi:10.15227/orgsyn.088.0102.
^ Robert M. Williams (2011). "4-Methoxy-4'-nitrophenyl. Recent Advances In The Stille Biaryl Coupling Reaction and Applications in Complex Natural Products Synthesis". Org. Synth. 88: 197–201. doi:10.15227/orgsyn.088.0197. PMC 3181114. PMID 21960729.

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[1] Kirchhoff, Jan H.; Netherton, Matthew R.; Hills, Ivory D.; Fu, Gregory C. (2002). "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". Journal of the American Chemical Society. 124 (46): 13662–13663. doi:10.1021/ja0283899. PMID 12431081.

[2] Denmark, Scott E.; Hung-Chang Liu, Jack (2011). "Discussion Addendum for: Palladium Catalyzed Cross-Coupling of (Z)-1-Heptenyldimethylsilanol with 4-Iodoanisole: (Z)-(1-Heptenyl)-4-methoxybenzene". Organic Syntheses. 88: 102. doi:10.15227/orgsyn.088.0102.

[3] Robert M. Williams (2011). "4-Methoxy-4'-nitrophenyl. Recent Advances In The Stille Biaryl Coupling Reaction and Applications in Complex Natural Products Synthesis". Org. Synth. 88: 197–201. doi:10.15227/orgsyn.088.0197. PMC 3181114. PMID 21960729.

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