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RESEARCH ARTICLE
Contents Vol 68(10)

Crystal Structure Studies towards the Synthesis and Applications of N-heterocyclic Carbene–Metal Complexes Derived from [2.2]Paracyclophane

Wenzeng Duan A C , Yudao Ma B D * , Yanmin Huo A and Qingxia Yao A
+ Author Affiliations
- Author Affiliations

A School of Chemistry and Chemical Engineering, Liaocheng University, Hunan Road No. 1, Liaocheng 252000, China.

B School of Chemistry and Chemical Engineering, Shandong University, Shanda South Road No. 27, Jinan 250100, China.

C School of Chemistry and Chemical Engineering, Taishan University, Tai’an 271021, China.

D Corresponding author. Email: ydma@sdu.edu.cn


Australian Journal of Chemistry 68(10) 1472-1478 https://doi.org/10.1071/CH15002
Submitted: 13 January 2015  Accepted: 9 March 2015   Published: 8 May 2015

Abstract

The crystal structures of six planar chiral N-heterocyclic carbene (NHC) precursors and one NHC–Rh complex derived from [2.2]paracyclophane were described. The NHC–metal complexes were prepared to examine their catalytic activities toward the Rh-catalyzed asymmetric addition of phenylboronic acid to 1-naphthaldehyde. The results were correlated to the single-crystal crystallographic studies. The novel NHC precursor 5 can achieve high catalytic activity in the asymmetric addition of phenylboronic acid to 1-naphthaldehyde.


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[19]  Crystal data for compound 3: C36H31Br2F3N2O3S, M 788.51, colourless block, orthorhombic, space group P 21 21 21, a 10.932(2), b 12.123(2), c 25.594(5) Å, β 90°, V 3391.9(11) Å3, Z 4, Dc 1.544 Mg m–3, F000 1592, MoKα radiation, μ 2.507 mm–1, T 296 K. 16581 data measured, of which 7446 unique (Rint 0.0954), θmax 27.50°, θmin 1.86°. Refinement of 7446 reflections (424 parameters) with I > 2σ(I) converged at final R1 0.0562 (R1 all data 0.2021), wR2 0.0973 (wR2 all data 0.1224), GoF 1.001. The structure was solved by the direct method and refined by the full-matrix least-squares method on F2 using the SHELXTL 97 crystallographic software package.

[20]  Crystal data for compound 5: C36H32BrCl3F2N2, M 714.08, colourless block, orthorhombic, space group P 2(1) 2(1) 2(1), a 11.703(5), b 11.958(5), c 23.535(10) Å, β = 90°, V = 3294(2) Å3, Z 28, Dc 1.446 Mg m–3, F000 1464, MoKα radiation, μ 1.532 mm–1, T 273 K. 16468 data measured, of which 5808 unique (Rint 0.0489), θmax 25.02°, θmin 1.91°. Refinement of 5808 reflections (397 parameters) with I > 2σ(I) converged at final R1 0.0421 (R1 all data 0.0780), wR2 0.0843 (wR2 all data 0.0962), GoF 0.990. The structure was solved by the direct method and refined by the full-matrix least-squares method on F2 using the SHELXTL 97 crystallographic software package.