Catalytic and stereoselective iodination of prochiral C-H bonds

Ramesh Giri, Xiao Chen, Xue Shi Hao, Jiao Jie Li, Jue Liang, Zi Peng Fan, Jin Quan Yu

Research output: Contribution to journalArticle

56 Citations (Scopus)

Abstract

Oxazolines were employed as cyclic chiral directing groups for stereoselective C-H activation. Oxazoline-directed cleavage of the β-C-H bonds followed by reaction with I2 gave a wide range of iodinated products. A large range of functional groups are tolerated. PdI2 was isolated in the reaction and found to be converted to Pd(OAc)2 upon treatment with a combination of I2 and PhI(OAc)2 in situ to achieve catalytic turnover. Diastereoselective iodination of prochiral C-H bonds were also investigated.

Original languageEnglish (US)
Pages (from-to)3502-3505
Number of pages4
JournalTetrahedron Asymmetry
Volume16
Issue number21
DOIs
StatePublished - Oct 31 2005

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Functional groups
Chemical activation
cleavage
activation
products
palladium(II) acetate

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Giri, R., Chen, X., Hao, X. S., Li, J. J., Liang, J., Fan, Z. P., & Yu, J. Q. (2005). Catalytic and stereoselective iodination of prochiral C-H bonds. Tetrahedron Asymmetry, 16(21), 3502-3505. https://doi.org/10.1016/j.tetasy.2005.08.049
Giri, Ramesh ; Chen, Xiao ; Hao, Xue Shi ; Li, Jiao Jie ; Liang, Jue ; Fan, Zi Peng ; Yu, Jin Quan. / Catalytic and stereoselective iodination of prochiral C-H bonds. In: Tetrahedron Asymmetry. 2005 ; Vol. 16, No. 21. pp. 3502-3505.
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abstract = "Oxazolines were employed as cyclic chiral directing groups for stereoselective C-H activation. Oxazoline-directed cleavage of the β-C-H bonds followed by reaction with I2 gave a wide range of iodinated products. A large range of functional groups are tolerated. PdI2 was isolated in the reaction and found to be converted to Pd(OAc)2 upon treatment with a combination of I2 and PhI(OAc)2 in situ to achieve catalytic turnover. Diastereoselective iodination of prochiral C-H bonds were also investigated.",
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Giri, R, Chen, X, Hao, XS, Li, JJ, Liang, J, Fan, ZP & Yu, JQ 2005, 'Catalytic and stereoselective iodination of prochiral C-H bonds', Tetrahedron Asymmetry, vol. 16, no. 21, pp. 3502-3505. https://doi.org/10.1016/j.tetasy.2005.08.049

Catalytic and stereoselective iodination of prochiral C-H bonds. / Giri, Ramesh; Chen, Xiao; Hao, Xue Shi; Li, Jiao Jie; Liang, Jue; Fan, Zi Peng; Yu, Jin Quan.

In: Tetrahedron Asymmetry, Vol. 16, No. 21, 31.10.2005, p. 3502-3505.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Catalytic and stereoselective iodination of prochiral C-H bonds

AU - Giri, Ramesh

AU - Chen, Xiao

AU - Hao, Xue Shi

AU - Li, Jiao Jie

AU - Liang, Jue

AU - Fan, Zi Peng

AU - Yu, Jin Quan

PY - 2005/10/31

Y1 - 2005/10/31

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AB - Oxazolines were employed as cyclic chiral directing groups for stereoselective C-H activation. Oxazoline-directed cleavage of the β-C-H bonds followed by reaction with I2 gave a wide range of iodinated products. A large range of functional groups are tolerated. PdI2 was isolated in the reaction and found to be converted to Pd(OAc)2 upon treatment with a combination of I2 and PhI(OAc)2 in situ to achieve catalytic turnover. Diastereoselective iodination of prochiral C-H bonds were also investigated.

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