Abstract
The Pd-mediated cross-coupling of (hetero)arenes with alkenes may be an effective method for the formation of a C–C bond from two C–H bonds. Discovered by Fujiwara and co-workers in 1967, this reaction led to a number of reports that we firstly highlighted in 2011 (review with references till June 2010) and for which, we retained the name “dehydrogenative Heck reaction”. The topic, especially the reactions of five-membered heteroarenes, has been the subject of intensive research over the last ten years. The present review is limited to these dehydrogenative Heck reactions published since 2010, underlining the progress of the procedures.
Highlights
Palladium-catalyzed C–H functionalization has been at the forefront of organic synthesis over the last half-century [1,2,3,4]
The above Fujiwara cross-coupling initially occurred with a very low palladium turnover [6], such dehydrogenation reactions, which could be named “Dehydrogenative Heck Reactions” (DHRs), have been the subject of intensive research over the last half century leading to efficient catalytic procedures
Especially in DMF/DMSO which is often used for DHR of five-membered heteroarenes (Equation heteroarenes (Equation (83))
Summary
Palladium-catalyzed C–H functionalization has been at the forefront of organic synthesis over the last half-century [1,2,3,4]. The above Fujiwara cross-coupling initially occurred with a very low palladium turnover [6], such dehydrogenation reactions, which could be named “Dehydrogenative Heck Reactions” (DHRs), have been the subject of intensive research over the last half century leading to efficient catalytic procedures. Liu’s team conditions carried out theCu(OAc) cross-coupling with allyl esters using Pd(OAc)2/Ag2CO3 in disclosed catalytic with 2 to regenerate active Pd species and CaCl2 as additive in DMSO/dioxane leading to a 88:12-99:1 mixture of linear and branched compounds via β-H elimination. The cross-coupling with allyl esters using Pd(OAc)2 /Ag2 CO3 in DMSO/dioxane leading to a 88:12-99:1 mixture of linear and branched compounds via β-H elimination rather than β-OCOR2 elimination (For such competitions, see [36]) (Equation (1)) [37]. Procedures associated various ligands reported for olefination acrylates, enones, acrylamides, styrenes, vinyl phosphonates, or sulfones (Equations (7).
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