Recyclable Palladium-Catalyzed Carbonylative Coupling of Aryl Halides and Organoaluminum Compounds with tert-Butyl Iso­cyanide as CO Equivalent Leading to 1,2-Diketones

Zhiyuan Tu; Jianan Zhan; Shengyong You; Mingzhong Cai

doi:10.1055/s-0040-1720121

Synthesis, Table of Contents

Synthesis 2024; 56(13): 2015-2024
DOI: 10.1055/s-0040-1720121

paper

Recyclable Palladium-Catalyzed Carbonylative Coupling of Aryl Halides and Organoaluminum Compounds with tert-Butyl Isocyanide as CO Equivalent Leading to 1,2-Diketones

Zhiyuan Tu

^aKey Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education and College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P. R. of China

,

Jianan Zhan

^aKey Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education and College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P. R. of China

,

Shengyong You∗

^bInstitute of Applied Chemistry, Jiangxi Academy of Sciences, Nanchang 330029, P. R. of China

,

Mingzhong Cai ∗

^aKey Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education and College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P. R. of China

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Abstract

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Abstract

An efficient heterogeneous palladium-catalyzed carbonylative coupling of aryl halides and organoaluminum compounds has been developed using tert-butyl isocyanide as CO equivalent. The carbonylation reaction proceeds smoothly in toluene with KO^tBu as a base at 100 °C by using 10 mol% of an SBA-15-anchored bidentate phosphine palladium(0) complex [2P-SBA-15-Pd(0)] as the catalyst and provides a general and practical approach for the assembly of 1,2-diketones in good to excellent yields. This heterogenized palladium catalyst can be readily separated and recovered via a simple centrifugation process and reused for more than seven cycles with almost consistent catalytic efficiency.

Key words

palladium - carbonylative coupling - organoaluminum reagents - 1,2-diketones - heterogeneous catalysis

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Supplementary Material

Supporting Information

Recyclable Palladium-Catalyzed Carbonylative Coupling of Aryl Halides and Organoaluminum Compounds with tert-Butyl Iso­cyanide as CO Equivalent Leading to 1,2-Diketones

Recyclable Palladium-Catalyzed Carbonylative Coupling of Aryl Halides and Organoaluminum Compounds with tert-Butyl Isocyanide as CO Equivalent Leading to 1,2-Diketones