Palladium‐catalyzed carbonylative coupling reactions of various N,N‐bis(methanesulfonyl)amides with arylboronic acids through C–N bond cleavage were carried out. The reactions proceeded under mild conditions in a short period of time without any additives to afford a wide range of unsymmetrical aryl ketones in excellent yields. This is the first example of a carbonylative coupling reaction using N,N‐bis(methanesulfonyl)amide as a coupling substrate.
Functionalized benzo[c]cinnoline derivatives were synthesized from easily accessible 2,2‐diamino‐1,1′‐biaryls using a nitrite source. In this simple process, various functional groups were tolerated under mild reaction conditions, and the practicality of the process was demonstrated through the gram‐scale production of the benzo[c]cinnolines.
We synthesized various carbazoles from anilines through a three-step process with good overall yields (up to 48%). This process comprises N-acetylation, copper(0)-mediated Ullmann homocoupling, and acid-mediated intramolecular amination. It permits various functional groups on the substrate. Scale-up of the developed three-step synthetic route to carbazoles was also demonstrated.
l-Ribose, a key precursor of various l-nucleosides can only be synthesized from other sugars or other non-sugar precursors. Herein, the study involves the synthesis of naturally rare l-ribose from readily available d-ribose. Though, many synthetic strategies are developed to meet the increasing demands of l-ribose, seeking innovation, a synthesis employing sequential lactonization as the key transformation was explored. This novel conversion involves protection, oxidation, sequential lactonization, reduction with DIBAL-H, and deprotection.
The competitive muscarinic receptor antagonist fesoterodine is a congener of tolterodine and has better efficiency compared to tolterodine. In this study, we present an efficient synthesis of the fesoterodine intermediate 3-(3-diisopropylamino-1-phenylpropyl)-4-hydroxybenzaldehyde from ethyl benzoylacetate by Friedel-Crafts alkylation in the presence of an acid as a key reaction step. The synthesis is carried out by the reduction of the ketoester to a 1,3-diol, diisopropylamine substitution, and Friedel-Crafts alkylation, followed by reduction and chiral resolution.
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