Palladium-catalyzed cross-coupling of aryldiazonium tetrafluoroborate salts with arylboronic esters
10.1016/s0040-4039(00)01076-5
Crossref journal-article
Elsevier BV
Tetrahedron Letters (78)
Bibliography

Willis, D. M., & Strongin, R. M. (2000). Palladium-catalyzed cross-coupling of aryldiazonium tetrafluoroborate salts with arylboronic esters. Tetrahedron Letters, 41(33), 6271–6274.

Authors 2
  1. Douglas M Willis (first)
  2. Robert M Strongin (additional)
References 23 Referenced 46
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  22. A mixture of desired product 3 and homocoupled by-products characteristically precipitates from these reactions under the described aqueous conditions.
  23. General procedure for cross-coupling of aryldiazonium tetrafluoroborate salts 1 and arylboronic esters 2. Aryldiazonium tetrafluoroborate salt (1.0 mmol), arylboronic ester (1.5 mmol), Na2PdCl4 (0.10 mmol) and CsF (1.5 mmol) were added to a reaction vessel purged thoroughly with N2 in the dark. Degassed 75% MeOH/H2O (2 mL) was added via syringe and the reaction was allowed to proceed at 40°C in a sand bath until completion. The solution was cooled to room temperature, concentrated, and the residue extracted with EtOAc (3×10 mL). The organic layer was dried with MgSO4, passed through Celite and the filtrate concentrated. Silica gel chromatography (pentane or 0–10% EtOAc in hexanes) afforded the respective biaryls, 3a–g, terphenyl 3h and naphthyl derivative 3i. Physical data for the cross-coupled products were consistent with the literature: the purity of each product was verified by GC/MS (tetradecane internal standard) and 1H NMR. Alkyl- and benzyldiazonium tetrafluoroborate salts were unreactive under these conditions.
Dates
Type When
Created 23 years, 1 month ago (July 25, 2002, 6:03 a.m.)
Deposited 5 years, 7 months ago (Jan. 7, 2020, 8:19 p.m.)
Indexed 1 year, 7 months ago (Jan. 20, 2024, 4:19 p.m.)
Issued 25 years, 1 month ago (Aug. 1, 2000)
Published 25 years, 1 month ago (Aug. 1, 2000)
Published Print 25 years, 1 month ago (Aug. 1, 2000)
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@article{Willis_2000, title={Palladium-catalyzed cross-coupling of aryldiazonium tetrafluoroborate salts with arylboronic esters}, volume={41}, ISSN={0040-4039}, url={http://dx.doi.org/10.1016/s0040-4039(00)01076-5}, DOI={10.1016/s0040-4039(00)01076-5}, number={33}, journal={Tetrahedron Letters}, publisher={Elsevier BV}, author={Willis, Douglas M and Strongin, Robert M}, year={2000}, month=aug, pages={6271–6274} }