Sp–sp3 C–C bond formation via Fe(OTf)3/TfOH cocatalyzed coupling reaction of terminal alkynes with benzylic alcohols

Abstract

An Fe(OTf)(3)/TfOH cocatalyzed sp-sp(3) C-C bond formation through the coupling of benzylic alcohols with terminal alkynes in the absence of base has been developed. H(2)O is the sole by-product.

Synthesis of tertiary arylamines: Lewis acid-catalyzed direct reductive N-alkylation of secondary amines with ketones through an alternative pathway

“…To trap carbocation intermediates upon reaction with suitable nucleophiles, substrates 16 and 19 were reacted under the optimized reaction conditions with nucleophiles such as thiol and alkyne (Scheme 3). 21,22 The formation of corresponding products in these cases clearly suggests that the current reaction is proceeding via a carbocationic pathway.…”

FeCl3‐ and GaCl3‐Catalyzed Dehydrative Coupling Reaction of Chromone‐Derived Morita‐Baylis‐Hillman Alcohols with Terminal Alkynes

“…Unfortunately, in the all cases the carbon-carbon triple bond was transformed to carbonyl group 8 or vinyl group. 9 Recently, Jiao and co-workers 10 reported Fe(OTf) 3 /TfOH-catalyzed coupling reaction of terminal alkynes with α-aryl benzylic alcohols, providing the only one example, in which the carbon-carbon triple bond was remained in the molecule of the product. However, the dehydrative coupling reaction of α-aryl allylic alcohols with terminal alkynes, in which the triple bond was remained in the product, was still elusive.…”

Iron-mediated cross dehydrogenative coupling (CDC) of terminal alkynes with benzylic ethers and alkanes

“…Recently, we report a Fe(OTf) 3 /TfOH cocatalyzed coupling reaction of terminal alkynes with benzylic alcohols in the absence of base for the sp-sp 3 C-C bond formation (Eq. (2)) [9]. When alcohols are employed as the alkyl electrophile, H 2 O becomes the sole byproduct, which makes this transformation atom efficient and environmentally benign.…”