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Chemical Communications | 2006

Selective functionalization of imidazoles via an iodine–copper exchange reaction

Xiaoyin Yang; Paul Knochel

The reaction of protected 4,5-diiodoimidazoles with (PhMe2CCH2)2CuLi regioselectively provides 5-cuprated imidazoles, which readily react with various electrophiles furnishing functionalized imidazoles in good yields; remarkably, these resulting mono-iodoimidazoles undergo again an iodine-copper exchange reaction in the presence of sensitive functional groups, like an aldehyde or a ketone.


Chemical Communications | 2006

Direct preparation of copper organometallics bearing an aldehyde function via an iodine-copper exchange.

Xiaoyin Yang; Paul Knochel

The iodine-copper exchange reaction allows the direct preparation of various aryl, heteroaryl and alkenyl cuprates bearing a formyl group, thus allowing a direct synthesis of polyfunctional aldehydes without the need of protecting groups or an additional oxidation step.


Synthesis | 2006

Stereoselective Preparation of Highly Functionalized (Z)-3-Copper Enoates by an Iodine-Copper Exchange Reaction

Xiaoyin Yang; Paul Knochel

3-Iodoenoates are readily converted into the corresponding alkenylcopper species with complete retention of configuration of the double bond via an iodine-copper exchange reaction. Quenching reactions with various electrophiles provide highly functionalized enoates in good yields.


Organic Letters | 2003

Successive iodine-magnesium or -copper exchange reactions for the selective functionalization of polyhalogenated aromatics.

Xiaoyin Yang; Thomas Rotter; Claudia Piazza; Paul Knochel


Organic Letters | 2004

Stereoselective SN2-Substitutions Using Polyfunctional Lithium Arylcuprates Prepared by an Iodine−Copper Exchange

M. Isabel Calaza; Xiaoyin Yang; and Darunee Soorukram; Paul Knochel


Organic Letters | 2004

Selective Functionalization in Positions 2 and 3 of Indole via an Iodine−Copper Exchange Reaction

Xiaoyin Yang; and Andreas Althammer; Paul Knochel


Organic Letters | 2006

Stereoselective functionalization of beta-iodo-alpha,beta-unsaturated ketones via an iodine-copper exchange reaction.

Xiaoyin Yang; Paul Knochel


Handbook of Functionalized Organometallics: Applications in Synthesis | 2008

Polyfunctional Organocopper Reagents for Organic Synthesis

Paul Knochel; Xiaoyin Yang; Nina Commermann


Synlett | 2004

Preparation and Acylation of Highly Functionalized Copper Derivatives of 3-Iodoindazoles Leading to Polyfunctional 3-Acylindazoles

Xiaoyin Yang; Paul Knochel


Synthesis | 2006

Preparation and Reactions of Functionalized Organocopper Reagents

Xiaoyin Yang; Paul Knochel

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