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

doi:10.1016/j.tetasy.2005.08.049

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

Chemistry

Research output: Contribution to journal › Article › peer-review

61 Scopus citations

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 language	English (US)
Pages (from-to)	3502-3505
Number of pages	4
Journal	Tetrahedron Asymmetry
Volume	16
Issue number	21
DOIs	https://doi.org/10.1016/j.tetasy.2005.08.049
State	Published - Oct 31 2005

All Science Journal Classification (ASJC) codes

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1016/j.tetasy.2005.08.049

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title = "Catalytic and stereoselective iodination of prochiral C-H bonds",

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.",

author = "Ramesh Giri and Xiao Chen and Hao, {Xue Shi} and Li, {Jiao Jie} and Jue Liang and Fan, {Zi Peng} and Yu, {Jin Quan}",

note = "Funding Information: We thank Brandeis University for financial support and the Camille and Henry Dreyfus Foundation for a New Faculty Award. ",

year = "2005",

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doi = "10.1016/j.tetasy.2005.08.049",

language = "English (US)",

volume = "16",

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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

N1 - Funding Information: We thank Brandeis University for financial support and the Camille and Henry Dreyfus Foundation for a New Faculty Award.

PY - 2005/10/31

Y1 - 2005/10/31

N2 - 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.

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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DO - 10.1016/j.tetasy.2005.08.049

M3 - Article

AN - SCOPUS:28044444568

SN - 0957-4166

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EP - 3505

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 21

ER -

Catalytic and stereoselective iodination of prochiral C-H bonds

Abstract

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