An explicit account of solvation is essential for modeling Suzuki–Miyaura coupling in protic solvents

An explicit account of solvation is essential for modeling Suzuki–Miyaura coupling in protic solvents Full article

Journal

Dalton Transactions
ISSN: 1477-9234 , E-ISSN: 1477-9226

Output data

Year: 2015, Volume: 44, Number: 40, Pages: 17795-17799 Pages count : 5 DOI: 10.1039/c5dt03126e

Authors

Zeifman Alexey A. ¹ , Novikov Fedor N. ¹ , Stroylov Victor S. ¹ , Stroganov Oleg V. ¹ , Svitanko Igor V. ¹ , Chilov Ghermes G. ¹

Affiliations

1	N. D. Zelinsky Institute Of Organic Chemistry (ZIOC RAS), Leninsky prospekt, 47, 119991 Moscow, Russian Federation

We compared explicit and implicit solvation approaches in modeling the free energy profile of the final step of Suzuki–Miyaura coupling. Both approaches produced similar ΔG≠ in all the studied solvents (benzene, toluene, DMF, ethanol, and water). Solvation free energies of individual reaction components reasonably correlated for explicit and implicit models in aprotic solvents (RMSE = 30–50 kJ mol−1, R2 > 0.71). However for ethanol and water the correlation was poor. We attributed this difference to the formation of the Pd⋯H–O hydrogen bond with Pd(PPh3)2 which was surprisingly observed in explicit modeling. Further QM calculations of the Pd(PPh3)2–H2O system confirmed the direction (Pd⋯H) and stability of this bonding. Therefore we stress the need for considering explicit solvation for modeling Pd-catalyzed reactions in protic solvents.

Zeifman A.A. , Novikov F.N. , Stroylov V.S. , Stroganov O.V. , Svitanko I.V. , Chilov G.G.
An explicit account of solvation is essential for modeling Suzuki–Miyaura coupling in protic solvents
Dalton Transactions. 2015. V.44. N40. P.17795-17799. DOI: 10.1039/c5dt03126e WOS Scopus OpenAlex

Web of science:	WOS:000362362500038
Scopus:	2-s2.0-84943523465
OpenAlex:	W2117627205

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