Liebeskind-Srogl cross-coupling reaction

Hintermann and his group prepared Soai aldehydes, 2-(alkynyl)-l,3-pyrimidine-5-carbaldehydes, in the absence of base, via a Liebeskind—Srogl cross-coupling reaction of terminal alkynes with 2-mercapto-l,3-pyrimi-dine-5-carbaldehyde (55) (Scheme 37) (140L1282). Optimal conditions for this synthesis were determined to be stirring of 1 equivalent of mer-captoaldehyde 55 with 1.5-2.0 equivalents of the terminal alkyne in a microwave reactor in the presence of 2.0 equivalents of copper(I)... 

The first example of a Liebeskind-Srogl cross-coupling reaction in water was reported (13JHC1368). Specifically, 2-(methylthio)pyridine and 2-(methylthio)benzothiazole were treated with a series of arylboronic acids in the presence of Pd(0) catalyst and thiophene-2-carboxylate. 

A series of new a-nucleophiles (738) has been synthesised, and their ability to efficiently and selectively cleave the P-S bond of organo-phosphorus nerve agents (737), has been evaluated. This reaction led to the new non-toxic phosphonic acid (739) and aminothiol (740) (Scheme 187). ° A series of novel pyrimidine based, acyclic nucleoside phosphonates (742), has been prepared, using the Liebeskind-Srogl cross-coupling protocol involving highly functionalised 2-(methylsulfanyl)pyrimidines (741) and various arylboronic acids (Scheme 188). " ... 

Prokopcova et al. (2005) performed thioether-boronic acid cross-coupling (Liebeskind-Srogl reaction) using microwave heating involving C-C cross-coupling... 

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