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Synthesis of Chiral Sulfoximines via Iridium‐Catalyzed Regio‐ and Enantioselective C−H Borylation: A Remarkable Sidearm Effect of Ligand

A rational-designed chiral bidentate boryl ligand (CBL) with a bulky side arm was effective in iridium-catalyzed regio-and enantioselective C−H borylation of N-silyl diaryl sulfoximines, affording a vast array of non-annulated chiral diaryl sulfoximines (39 examples) with high enantioselectivities (up to 96 %). DFT calculations revealed that the side arm was critical to confer high regio- and enantioselectivity by virtue of the steric effect.


Abstract

Transition metal-catalyzed enantioselective C−H activation of prochiral sulfoximines for non-annulated products remains a formidable challenge. We herein report iridium-catalyzed enantioselective C−H borylation of N-silyl diaryl sulfoximines using a well-designed chiral bidentate boryl ligand with a bulky side arm. This method is capable of accommodating a broad range of substrates under mild reaction conditions, affording a vast array of chiral sulfoximines with high enantioselectivities. We also demonstrated the synthetic utility on a preparative-scale C−H borylation for diverse downstream transformations, including the synthesis of chiral version of bioactive molecules. Computational studies showed that the bulky side arm of the ligand confers high regio- and enantioselectivity through steric effect.

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