Abstract
Minisci-type reactions constitute one of the most powerful methods for building up complexity around basic heteroarenes. The most desirable variants involve formal oxidative coupling of a C–H bond on each partner, leading back to the simplest possible starting materials. We herein disclose a method that enables such a coupling of linear amides and heteroarenes with full control of enantioselectivity at the newly formed stereocenter as well as site selectivity on both the heteroarene and the amide. This is achieved by the use of a chiral phosphoric acid catalyst in conjunction with diacetyl as a combined hydrogen atom transfer reagent and oxidant. Diacetyl is directly photoexcitable, and thus, no extraneous photocatalyst is required: an added feature that contributes to the simplicity and practicality of the protocol.
Highlights
Minisci-type reactions constitute one of the most powerful methods for building up complexity around basic heteroarenes
M ethods for the selective conversion of C−H bonds to new functional groups are in great demand due to the efficiency and diversity that they can impart, with vast progress being made through a variety of mechanisms
Often referred to as oxidative coupling or cross-dehydrogenative coupling reactions, these processes encompass a great breadth of mechanistic diversity, the common feature being that the formal loss of hydrogen necessitates an oxidant.[1−12] In many cases a stereocenter is created, and exerting control over its formation represents an appealing way to increase the value added by the methodology even further
Summary
Minisci-type reactions constitute one of the most powerful methods for building up complexity around basic heteroarenes.
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