Abstract
Since the first report and due to its handiness and wide scope, the Suzuki-Miyaura (SM) cross coupling reaction has become a routine methodology in many laboratories worldwide. With respect to other common transition metal catalyzed cross couplings, the SM reaction has been so far less exploited as a tool to introduce an acyl function into a specific substrate. In this review, the various approaches found in the literature will be considered, starting from the direct SM acylative coupling to the recent developments of cross coupling between boronates and acyl chlorides or anhydrides. Special attention will be dedicated to the use of masked acyl boronates, alkoxy styryl and alkoxy dienyl boronates as coupling partners. A final section will be then focused on the acyl SM reaction as key synthetic step in the framework of natural products synthesis.
Highlights
The introduction of acyl functionalities represents a fruitful and widespread tool to construct building blocks for the synthesis of natural products and pharmaceutical compounds, and a number of Molecules 2013, 18 approaches are well known among the synthetic organic chemistry community [1,2]
Gooßen and coworkers reported an efficient method for the catalyzed SM-cross coupling of carboxylic acids to arylboronic acids in the presence of palladium(II) acetate (Scheme 8) [34]
Despite the direct acylation of organoboron derivatives has proved to be an attractive approach to the formation of symmetric and unsymmetrically substituted ketones, the carbonylative Pd-catalyzed coupling reaction has been widely employed for the synthesis of aromatic ketones [12]
Summary
The introduction of acyl functionalities represents a fruitful and widespread tool to construct building blocks for the synthesis of natural products and pharmaceutical compounds, and a number of Molecules 2013, 18 approaches are well known among the synthetic organic chemistry community [1,2]. One potential approach is the Friedel-Crafts acylation of substituted aromatic rings [3,4,5] This method entails some problems and limitations such as drastic reaction conditions, low regioselectivity, and a large amount of by-products [6]. Suzuki-Miyaura cross-coupling has been successfully exploited to introduce an acyl function onto a specific substrate with high regioselectivity. The first of them is the palladium-catalyzed cross-coupling reaction of arylboronic acids with carboxylic acid derivatives (see Section 2), and are based on the cleavage of the C–O bond of the carboxylic derivative in the presence of palladium catalyst This approach is superior to the previous methods in terms of reaction conditions, efficiency, and functional group compatibility. The intent of this short review is to give a general overview of the most recent advances in the literature in this field
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