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α-Amidoboronate esters by amide-directed alkane C H borylation

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Abstract α-Amidoboronic acids have received significant attention in recent years following the development of Bortezomib as an FDA-approved treatment of multiple myeloma and mantle cell lymphoma. More versatile methods to… Click to show full abstract

Abstract α-Amidoboronic acids have received significant attention in recent years following the development of Bortezomib as an FDA-approved treatment of multiple myeloma and mantle cell lymphoma. More versatile methods to access α-amidoboronic acids continue to be developed. A direct method to access the precursors, α-amidoboronate esters, by iridium-catalyzed C H borylation of amides was developed using a readily available ligand/catalyst combination. Although the scope is limited, good yields of α-amidoboronate esters are achieved in high selectivity. Conversion of the boronate esters to the corresponding α-amidoboronic acids was also demonstrated.

Keywords: directed alkane; amidoboronic acids; amide directed; esters amide; amidoboronate esters; borylation

Journal Title: Tetrahedron Letters
Year Published: 2019

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