Corrigendum to: Highly Convenient, Clean, Fast, and Reliable Sonogashira Coupling Reactions Promoted by Aminophosphine-Based Pincer Complexes of Palladium Performed under Additive- and Amine-Free Reaction Conditions (Advanced Synthesis & Catalysis, (2009), 351, 6, (891-902), 10.1002/adsc.200900112);Highly convenient, clean, fast, and reliable Sonogashira coupling reactions promoted by aminophosphine-based pincer complexes of palladium performed under additive-and amine-free reaction conditions

Advanced Synthesis and Catalysis

Volumn 351, Issue 6, 2009, Pages 891-902

  Bolliger, Jeanne L ^a   Frech, Christian M ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

C C coupling; Cross coupling; Palladium; Pincer complexes; CC coupling; cross coupling; pincer complexes; palladium

Indexed keywords

EID: 65249128696     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200990018     Document Type: Erratum

References (139)

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121. See Experimental Section.
122. No difference in the performance of the Sonogashira reaction was observed when ethylene glycol of various qualities (with up to 5% of water) was used.
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125. [26]
126. It should be mentioned that also 3-ethynylpyridine undergoes slow formation of 3-(1,3-dioxolan-2-ylmethyl)-pyridine with ethylene glycol under catalytic reaction conditions. This side-reaction, however, only lead to significant amounts of 3-(1,3-dioxolan-2-ylmethyl)pyri-dine in slow Sonogashira cross-coupling reactions, as it is for instance the case when 4-iodoaniline (see Table 3, entry 8) was used as coupling partner, explaining the relatively low product yield obtained.
127. In contrast to reactions examined with aryl iodides, where no side-products were detectable, small amounts of homocoupling was observed in some of the reactions performed with aryl bromides. Thus, in order to maximize the product yields the reactions were generally performed with 1.5 equivalents (relative to aryl bromide) of alkyne.
128. Coupling reactions performed with 3-ethynylpyridine and 5-ethynyl-1-methyl-1H-imidazole and aryl bromides as coupling partners were only of limited success, since the formation of side-products, such as 3-(1,3-di-oxolan-2-ylmethyl)pyridine became dominant.
129. Aryl trifluoromethanesulfonates are sensitive towards moisture and hence, are expected to be incompatible with our reaction protocol. Indeed, no coupling products were formed, clean conversions into their corresponding phenols occurred instead.
130. See graph S1 in the Supporting Information.
131. [21b] The reason for the effect of water on the induction period could be explained by a faster decomposition of the pincer core. However, no effect on the induction period was noticed. The addition of large amounts of water (~10%), however, could result in the partial decomposition of the catalyst and would provide an explanation for the slower conversions observed.
132. For a comprehensive review article about the problem of distinguishing true homogeneous catalysis from soluble or other metal-particle heterogeneous catalysis under reducing conditions see: J. A. Widegren, R. G. Finke, J. Mol. Catal. A 2003, 198, 317 and references cited therein.
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137. This result was expected to be obtained, since 2-iodo-thiophene was successfully coupled with ethynylbenzene and 2-ethynyl-6-methoxynaphthalene (see Table 1, entry 24 and Table 2, entry 10).
138. [21b]
139. It should be noted that NMR investigations were not conclusive and the transformation of 1 (or 2) into another, catalytically active species could not be confirmed by NMR spectroscopy.