Issue 6, 2018

Formation of macrocyclic ring systems by carbonylation of trifunctional P/B/B frustrated Lewis pairs

Abstract

The trifunctional P/B/B frustrated Lewis pairs 11a–c featuring bulky aryl groups at phosphorus [Dmesp (a), Tipp (b), Mes* (c)] react with H2 by heterolytic hydrogen splitting followed by cleavage of HB(C6F5)2 to give the zwitterionic six-membered heterocyclic PH phosphonium/borate products 14a–c. Compounds 11a,b react with carbon monoxide by means of a Lewis acid induced CO insertion/rearrangement sequence that eventually results in the formation of the macrocyclic dimers 17a,b. The respective carbonylation reaction of the Mes*P/B/B FLP gives the macrocyclic trimer 18c. The new products were characterized spectroscopically and by X-ray diffraction and the reaction mechanism was analyzed by DFT calculations.

Graphical abstract: Formation of macrocyclic ring systems by carbonylation of trifunctional P/B/B frustrated Lewis pairs

Supplementary files

Article information

Article type
Edge Article
Submitted
10 Oct 2017
Accepted
13 Dec 2017
First published
14 Dec 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 1544-1550

Formation of macrocyclic ring systems by carbonylation of trifunctional P/B/B frustrated Lewis pairs

L. Wang, S. Dong, C. G. Daniliuc, L. Liu, S. Grimme, R. Knitsch, H. Eckert, M. R. Hansen, G. Kehr and G. Erker, Chem. Sci., 2018, 9, 1544 DOI: 10.1039/C7SC04394E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements