Photoinduced Metal‐Free Decarboxylative Transformations: Rapid Access to Amines, Alkyl Halides, and Olefins
Herein, we described a versatile photocatalytic strategy for the decarboxylative transformations of redox-active esters (RAE) to a variety of alkyl halides, amines, and olefins in the presence of nBu4NI in a single-step. It is a straightforward method which is applied to the functionalization of a series of primary, secondary, and tertiary aliphatic carboxylic acid derivatives and complex natural products. Mechanistically, a charge transfer complex (CTC) was formed through non-covalent interaction between RAE and nBu4NI. Upon photoexcitation, the ammonia salt acted as both an efficient electron donor and an iodine source for radical recombination. The mild reaction condition allows this method can be applied for modification of complex natural products and versatile follow-up transformations.
Herein, we report an efficient photocatalytic strategy for the decarboxylative transformations of redox-active esters to construct C=C, C(sp3)−N, and C(sp3)−X bonds in a single-step. This operationally simple method provides a straightforward access to a variety of protected alkyl amines, alkyl halides and olefins under mild conditions in the absence of metals and photocatalysts. The method can successfully be applied to primary, secondary, and tertiary aliphatic carboxylic acid derivatives. Mechanistic studies indicate that the charge transfer complex (CTC) was formed by nBu4NI with redox-active esters, in which the nBu4NI acted as both an iodine source and an efficient electron donor.
Wiley: European Journal of Organic Chemistry: Table of Contents
Authors: Jia‐jing Luo, Dong Jing, Cong Lu, Ke Zheng