Rhodium(III)‐Catalyzed Activation of C sp 3H Bonds and Subsequent Intermolecular Amidation at Room Temperature1. Issue 32 (15th July 2015)

• Record Type: Journal Article
• Authors: Huang, Xiaolei; Wang, Yan; Lan, Jingbo; You, Jingsong
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 32(2015)
• Page Start: 9404
• Page End: 9408
• Publication Date: 2015-07-15
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201504507
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Disclosed herein is a Rh<sup>III</sup>‐catalyzed chelation‐assisted activation of unreactive C<inline-formula><alternatives><inline-graphic mimetype="image" xlink:href="ark:/27927/pgj270cczsc" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /><mml:math altimg="urn:x-wiley:14337851:media:ANIE201504507:tex2gif-inf-2" overflow="scroll" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:msub><mml:mtext> </mml:mtext><mml:mrow><mml:mtext>sp</mml:mtext><mml:msup><mml:mtext> </mml:mtext><mml:mrow><mml:mtext>3</mml:mtext></mml:mrow></mml:msup></mml:mrow></mml:msub></mml:math></alternatives></inline-formula>H bonds, thus enabling an intermolecular amidation to provide a practical and step‐economic route to 2‐(pyridin‐2‐yl)ethanamine derivatives. Substrates with other N‐donor groups are also compatible with the amidation. This protocol proceeds at room temperature, has a relatively broad functional‐group tolerance and high selectivity, and demonstrates the potential of rhodium(III) in the promotive functionalization of unreactive C<inline-formula><alternatives><inline-graphic mimetype="image" xlink:href="ark:/27927/pgj270ccztx" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /><mml:math altimg="urn:x-wiley:14337851:media:ANIE201504507:tex2gif-inf-3" overflow="scroll" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:msub><mml:mtext> </mml:mtext><mml:mrow><mml:mtext>sp</mml:mtext><mml:msup><mml:mtext> </mml:mtext><mml:mrow><mml:mtext>3</mml:mtext></mml:mrow></mml:msup></mml:mrow></mml:msub></mml:math></alternatives></inline-formula>H bonds. A rhodacycle having a SbF<sub>6</sub><sup>−</sup> counterion was identified as a plausible intermediate.</p> </abstract>