Synthesis 2023; 55(11): 1690-1699
DOI: 10.1055/a-1970-4520
paper
Special Issue dedicated to Prof. Cristina Nevado, recipient of the 2021 Dr. Margaret Faul Women in Chemistry Award

Versatile Synthesis of Trisphosphines Bearing Phenylene and Vinylene Backbones Useful for Metal Catalysis and Materials Applications

Takahiro Doba
,
Shota Fukuma
,
Rui Shang
,
Eiichi Nakamura
We thank Mitsubishi Chemical Corporation for partial financial support. This research is supported by Ministry of Education, Culture, Sports, Science and Technology (MEXT) KAKENHI grant number 19H05459 (to E.N.) and Japan Society for the Promotion of Science (JSPS) KAKENHI grant number 19K15555 (to R.S.). T.D. thanks Japan Society for the Promotion of Science for the predoctoral fellowship.


Abstract

Trisphosphines, in which two phenylene or vinylene backbones connect three phosphine atoms, belong to an emerging class of ligands in metal-catalyzed organic synthesis and materials applications. However, these ligands were previously known only in a small variety because of the synthetic limitations. We report herein two versatile synthetic routes to a hitherto unavailable variety of trisphosphines. The compounds bearing phenylene backbones were synthesized by sequential addition of two different organolithium reagents to triphenyl phosphite and that with vinylene backbones by stereoretentive addition of lithium diarylphosphide to a cis-bromoalkene. The new trisphosphine compounds will serve as valuable tools for the development of transition-metal-catalyzed reactions and functional materials.

Supporting Information



Publication History

Received: 26 July 2022

Accepted after revision: 31 October 2022

Accepted Manuscript online:
31 October 2022

Article published online:
23 November 2022

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