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Propargylic Substitution, Propargylation

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A catalytic asymmetric Negishi cross-coupling of racemic secondary propargylic halides with arylzinc reagents has been developed using commerically available catalyst components (NiCl2·glyme and pybox as ligand).
S. W. Smith, G. C. Fu, J. Am. Chem. Soc., 2008, 130, 12645-12647.


A copper-catalyzed substitution reaction of propargylic ammonium salts with aryl Grignard reagents is stereospecific and α-regioselective and proceeds with exceptional functional group tolerance.
M. Guisán-Ceinos, V. Martín-Heras, M. Tortosa, J. Am. Chem. Soc., 2017, 139, 8448-8451.


LaCl3·2LiCl catalyzes a propargylation of Grignard reagents in the absence of ligand in high regioselectivity and stereospecificity. The approach shows a wide substrate scope using alkyl or (hetero)aryl Grignard reagents and alkynyl electrophiles with different leaving groups. This protocol was further applied for the formal synthesis of frondosin B.
D. Sun, T. Rajeshkumar, Y. Li, J. Xu, R. Chen, Z. Wan, Z. Lv, L. Maron, Y.-H. Chen, Org. Lett., 2023, 25, 6730-6735.


A chiral sulfinamide phosphine ligand enables a Pd-catalyzed enantioselective three-component coupling of N-tosylhydrazones, aryl halides, and terminal alkynes under mild conditions utilizing (GF-Phos) to provide chiral diarylmethyl alkynes. This reaction features readily available starting materials, general substrate scope, high enantioselectivity, and ease of scale-up.
G. Zhao, Y. Wu, H.-H. Wu, J. Yang, J. Zhang, J. Am. Chem. Soc., 2021, 143, 17983-17988.


PMA-silica gel catalyzes efficiently the propargylation of aromatic compounds with arylpropargyl alcohols in the absence of solvent under environmentally benign conditions.
P. Srihari, J. S. S. Reddy, S. S. Mandal, K. Satyanarayana, J. S. Yadav, Synthesis, 2008, 1853-1860.


p-Toluenesulfonic acid efficiently catalyzes direct nucleophilic substitutions of the hydroxy groups of propargylic alcohols with a large variety of carbon- and heteroatom-centered nucleophiles. Reactions can be conducted under mild conditions and in air without the need for dried solvents.
R. Sanz, A. Martinez, J. M. Alvarez-Gutierrez, F. Rodriquez, Eur. J. Org. Chem., 2006, 1383-1386.


A general and efficient FeCl3-catalyzed substitution reaction of propargylic alcohols with carbon- and heteroatom-centered nucleophiles such as allyl trimethylsilane, alcohols, aromatic compounds, thiols, and amides, forms new C-C, C-O, C-S and C-N bonds.
Z.-P. Zhan, J.-L. Yu, Y.-Y. Cui, R.-F. Yang, W.-Z. Yang, J.-P. Li, J. Org. Chem., 2006, 71, 8298-8301.