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Issue 1, 2012

Chloro- and phenoxy-phosphines in frustrated Lewis pair additions to alkynes

Author affiliations

Abstract

The reaction of tBu(C6H4O2)P, with the borane B(C6F5)3 gives rise to NMR data consistent with the formation of the classical Lewis acid–base adduct tBu(C6H4O2)P(B(C6F5)3) (1). In contrast, the NMR data for the corresponding reactions of tBu(C20H12O2)P and Cl(C20H12O2)P with B(C6F5)3 were consistent with the presence of equilibria between free phosphine and borane and the corresponding adducts. Nonetheless, in each case, the adducts tBu(C20H12O2)P(B(C6F5)3) (2) and Cl(C20H12O2)P(B(C6F5)3) (3) were isolable. The species 1 reacts with PhCCH to give the new species tBu(C6H4O2)P(Ph)C[double bond, length as m-dash]CHB(C6F5)3 (4) in near quantitative yield. In an analogous fashion, the addition of PhCCH to solutions of the phosphinestBu(C20H12O2)P, tBuPCl2 and (C6H3(2,4-tBu2)O)3P each with an equivalent of B(C6F5)3 gave rise to L(Ph)C[double bond, length as m-dash]CHB(C6F5)3 (L = tBu(C20H12O2)P5, tBuPCl26 and (C6H3(2,4-tBu2)O)3P 7). X-Ray data for 1, 2, 6 and 7 are presented. The implications of these findings are considered.

Graphical abstract: Chloro- and phenoxy-phosphines in frustrated Lewis pair additions to alkynes

Supplementary files

Article information


Submitted
23 Jun 2011
Accepted
16 Aug 2011
First published
08 Sep 2011

Dalton Trans., 2012,41, 237-242
Article type
Paper

Chloro- and phenoxy-phosphines in frustrated Lewis pair additions to alkynes

C. B. Caputo, S. J. Geier, E. Y. Ouyang, C. Kreitner and D. W. Stephan, Dalton Trans., 2012, 41, 237 DOI: 10.1039/C1DT11196E

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