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Trichlorophenyl Formate: Highly Reactive and Easily Accessible Crystalline CO Surrogate for Palladium-Catalyzed Carbonylation of Aryl/Alkenyl Halides and Triflates
Organic Letters ( IF 4.9 ) Pub Date : 2012-09-28 00:00:00 , DOI: 10.1021/ol302593z
Tsuyoshi Ueda 1 , Hideyuki Konishi 1 , Kei Manabe 1
Affiliation  

The high utility of 2,4,6-trichlorophenyl formate, a highly reactive and easily accessible crystalline CO surrogate, is demonstrated. The decarbonylation with NEt3 to generate CO proceeded rapidly at rt, thereby allowing external-CO-free Pd-catalyzed carbonylation of aryl/alkenyl halides and triflates. The high reactivity of the CO surrogate enabled carbonylation at rt and significantly reduced the quantities of formate to near-stoichiometric levels. The obtained trichlorophenyl esters can be readily converted to a variety of carboxylic acid derivatives in high yields.

中文翻译:

三氯苯基甲酸酯:高活性和易于获得的结晶CO替代物,用于钯催化的芳基/烯基卤化物和三氟甲磺酸酯的羰基化反应

证明了2,4,6-三氯苯基甲酸的高实用性,这是一种高反应性且易于获得的结晶CO替代物。用NEt 3脱羰以生成CO在室温下迅速进行,从而实现了无外部CO-Pd催化的芳基/烯基卤化物和三氟甲磺酸酯的羰基化反应。CO替代物的高反应活性可实现rt处的羰基化,并将甲酸的量显着降低至接近化学计量的水平。所获得的三氯苯基酯可以容易地以高收率转化为多种羧酸衍生物。
更新日期:2012-09-28
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