Display options
Cite
IJpeij EG, Beijer FH, Arts HJ, et al. A Suzuki coupling based route to 2,2'-bis(2-indenyl)biphenyl derivatives. J Org Chem. 2002;67(1):169-76doi: 10.1021/jo016040i.
IJpeij, E. G., Beijer, F. H., Arts, H. J., Newton, C., de Vries, J. G., & Gruter, G. J. (2002). A Suzuki coupling based route to 2,2'-bis(2-indenyl)biphenyl derivatives. The Journal of organic chemistry, 67(1), 169-76. https://doi.org/10.1021/jo016040i
IJpeij, Edwin G, et al. "A Suzuki coupling based route to 2,2'-bis(2-indenyl)biphenyl derivatives." The Journal of organic chemistry vol. 67,1 (2002): 169-76. doi: https://doi.org/10.1021/jo016040i
IJpeij EG, Beijer FH, Arts HJ, Newton C, de Vries JG, Gruter GJ. A Suzuki coupling based route to 2,2'-bis(2-indenyl)biphenyl derivatives. J Org Chem. 2002 Jan 11;67(1):169-76. doi: 10.1021/jo016040i. PMID: 11777455.
Copy Download .nbib Format: NLM
Share it on

J Org Chem. 2002 Jan 11;67(1):169-76. doi: 10.1021/jo016040i.

A Suzuki coupling based route to 2,2'-bis(2-indenyl)biphenyl derivatives.

The Journal of organic chemistry

Edwin G IJpeij, Felix H Beijer, Henricus J Arts, Claire Newton, Johannes G de Vries, Gert-Jan M Gruter

Affiliations

  1. DSM Research, Department of Polyolefins, Chemistry and Catalysis, P.O. Box 18, 6160 MD Geleen, The Netherlands. [email protected]

PMID: 11777455 DOI: 10.1021/jo016040i

Abstract

Because of the promising performance in olefin polymerization of 2,2'-bis(2-indenyldiyl)biphenyl zirconium dichloride, we developed a new and broadly applicable route to 2,2'-bis(2-indenyl)biphenyl derivatives. Reaction of the known 2,2'-diiodobiphenyl (26) with the new 2-indenyl boronic acid (23) did not result in the desired 2,2'-bis(2-indenyl)biphenyl (10); instead an isomer thereof, (spiro-1,1-(2,2'-biphenyl)-2-(2-indenyl)indane) (27), was obtained. It was found that compound 10 could be made via a palladium-catalyzed reaction of 2,2-biphenyldiboronic acid (31) with 2-bromoindene (21) under standard Suzuki reaction conditions. However, the yield of this reaction was low at low palladium catalyst loadings, due to a competitive hydrolysis reaction of 2,2-biphenyldiboronic acid (31). HTE techniques were used to find an economically viable protocol. Thus, use of the commercially available 1.0 molar solution of (n-Bu)(4)NOH in methanol with cosolvent toluene led to precipitation of the pure product in a fast and clean reaction, using only 0.7 mol % (0.35 mol % per C-C) of the expensive palladium catalyst.

Publication Types