SnCl2-mediated carbonyl allylation in fully aqueous media

Tan, Xiang-Hui; Hou, Yongquan; Huang, Chao; Liu, Lei; Guo, Qing‐Xiang

doi:10.1016/j.tet.2004.05.046

Cited by 43 publications

(9 citation statements)

References 72 publications

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“…12 TiCl 3 is commercially available and can be synthesized by dissolving titanium in aqueous hydrochloric acid.…”

Section: Introductionmentioning

confidence: 99%

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Titanium(III) Trichloride

2012

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“…12 TiCl 3 is commercially available and can be synthesized by dissolving titanium in aqueous hydrochloric acid.…”

Section: Introductionmentioning

confidence: 99%

“…11 Apart from these applications, TiCl 3 is also known as a Lewis acid to catalyze the SnCl 2 -mediated Barbier reactions between aldehydes and allyl halides in aqueous media. 12 TiCl 3 is commercially available and can be synthesized by dissolving titanium in aqueous hydrochloric acid.…”

Section: Introductionmentioning

confidence: 99%

Titanium(III) Trichloride

2012

Synlett

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“…[1][2][3] Various other catalytic and/or synergic roles of SnCl 2 have also been demonstrated recently on numerous occasions, such as, in the palladium-catalyzed cyclocarbonylation of monoterpenes, 4 the PdCl 2 / SnCl 2 electrodeless deposition of copper on micronic NiTi shape memory alloy particles, 5 the mild, ecofriendly and fast reductions of nitroarenes to aminoarenes using stannous dichloride dihydrate in ionic liquid tetrabutylammonium bromide, 6 and the SnCl 2 -mediated carbonyl allylation reaction between aldehydes and allyl halides in fully aqueous media. 7 More relevant to the present study, however, is the role of SnCl 2 in the semiconductor gas sensor industry [8][9][10] specifically in the process of chemical vapor deposition ͑CVD͒. 11,12 For instance, SnO 2 thin films with uniform thickness or fine par-ticles with uniform size used in gas sensors are often produced in high temperature gas-phase processes, e.g., CVD, high-temperature flow reactors, and flames.…”

Section: Introductionmentioning

confidence: 99%

Ab initio calculations on SnCl2 and Franck-Condon factor simulations of its ã-X̃ and B̃-X̃ absorption and single-vibronic-level emission spectra

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et al. 2007

The Journal of Chemical Physics

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Confirmed assignments of isomeric dimethylbenzyl radicals generated by corona discharge J. Chem. Phys. 135, 214305 (2011) Photodissociation of methyl iodide embedded in a host-guest complex: A full dimensional (189D) quantum dynamics study of CH3I@resorc [4]arene J. Chem. Phys. 135, 184102 (2011) Computational study of the interaction of indole-like molecules with water and hydrogen sulfide J. Chem. Phys. 135, 134310 (2011) Communication: Rigorous calculation of dissociation energies (D0) of the water trimer, (H2O)3 and (D2O)3 J. Chem. Phys. 135, 131101 (2011) Additional information on J. Chem. Phys. Minimum-energy geometries, harmonic vibrational frequencies, and relative electronic energies of some low-lying singlet and triplet electronic states of stannous dichloride, SnCl 2 , have been computed employing the complete-active-space self-consistent-field/multireference configuration interaction ͑CASSCF/MRCI͒ and/or restricted-spin coupled-cluster single-double plus perturbative triple excitations ͓RCCSD͑T͔͒ methods. The small core relativistic effective core potential, ECP28MDF, was used for Sn in these calculations, together with valence basis sets of up to augmented correlation-consistent polarized-valence quintuple-zeta ͑aug-cc-pV5Z͒ quality. Effects of outer core electron correlation on computed geometrical parameters have been investigated, and contributions of off-diagonal spin-orbit interaction to relative electronic energies have been calculated. In addition, RCCSD͑T͒ or CASSCF/MRCI potential energy functions of the X 1 A 1 , ã 3 B 1 , and B 1 B 1 states of SnCl 2 have been computed and used to calculate anharmonic vibrational wave functions of these three electronic states. Franck-Condon factors between the X 1 A 1 state, and the ã 3 B 1 and B 1 B 1 states of SnCl 2 , which include anharmonicity and Duschinsky rotation, were then computed, and used to simulate the ã-X and B -X absorption and corresponding single-vibronic-level emission spectra of SnCl 2 which are yet to be recorded. It is anticipated that these simulated spectra will assist spectroscopic identification of gaseous SnCl 2 in the laboratory and/or will be valuable in in situ monitoring of SnCl 2 in the chemical vapor deposition of SnO 2 thin films in the semiconductor gas sensor industry by laser induced fluorescence and/or ultraviolet absorption spectroscopy, when a chloride-containing tin compound, such as tin dichloride or dimethyldichlorotin, is used as the tin precursor.

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“…Guo et al reported the SnCl 2 -mediated carbonyl allylation in aqueous media using various Lewis acid additives. [20] The development of more improved synthetic methods for the preparation of homoallylic alcohols remains an active research area.…”

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confidence: 99%

“…Nitrobenzaldehyde gave the desired product in excellent yields without reduction of nitro group (Table 3, entry 3). Aliphatic aldehydes such as propionaldehyde, heptaldehyde and cyclohexanecarboxaldehyde gave satisfactory yields with longer reaction times (Table 3, entries [20][21][22]. Nevertheless, the CuFAP-catalyzed allylation does not work efficiently for ketones.…”

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confidence: 99%