2016
DOI: 10.1021/jacs.5b11889
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Discovery and Computational Rationalization of Diminishing Alternation in [n]Dendralenes

Abstract: The [n]dendralenes are a family of acyclic hydrocarbons which, by virtue of their ability to rapidly generate structural complexity, have attracted significant recent synthetic attention. [3]Dendralene through [8]dendralene have been previously prepared but no higher member of the family has been reported to date. Here, we describe the first chemical syntheses of the "higher" dendralenes, [9]dendralene through [12]dendralene. We also report a detailed investigation into the spectroscopic properties and chemica… Show more

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Cited by 28 publications
(47 citation statements)
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“…In this regard, they are well configured to maximize "step economy" en route to both natural and unnatural materials that contain polycyclic arrays. Notwithstanding the remarkable advances made in preparing higher homologs that now have reached [12]dendralene, [4] recent papers from the Sherburn group highlight the need for additional inroads to both the parent and especially substituted systems, as well as new chemistry that extends the repertoire of reactions of dendralenes beyond [4+2] cycloadditions. Indeed, in a recent Account, [5] Sherburn concludes: "Regarding our deployment of the dendralenes and related unsaturated hydrocarbons in the rapid generation of structural complexity, again, we have deployed only known reactions (and in the main, just one: the venerable Diels-Alder reaction)."…”
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confidence: 99%
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“…In this regard, they are well configured to maximize "step economy" en route to both natural and unnatural materials that contain polycyclic arrays. Notwithstanding the remarkable advances made in preparing higher homologs that now have reached [12]dendralene, [4] recent papers from the Sherburn group highlight the need for additional inroads to both the parent and especially substituted systems, as well as new chemistry that extends the repertoire of reactions of dendralenes beyond [4+2] cycloadditions. Indeed, in a recent Account, [5] Sherburn concludes: "Regarding our deployment of the dendralenes and related unsaturated hydrocarbons in the rapid generation of structural complexity, again, we have deployed only known reactions (and in the main, just one: the venerable Diels-Alder reaction)."…”
mentioning
confidence: 99%
“…Other reactions of functionalized dendralenes, especially those associated with higher homologs that are regioselective, are few in number. [2d, 5] Since most published routes to dendralenes involve double cross-couplings from dihalo-and diborylated intermediates (Figure 2, top) [4,6] selective mono-functionalized and unsymmetrical patterns, which are likely to prove more valuable in total synthesis, remain few in number. In this report, therefore, we describe rapid access to both functionalized symmetrical and unsymmetrical [3]-[6]dendralenes from a common allenic precursor, using Pd-catalyzed crosscouplings under micellar catalysis conditions; i.e., in water and typically at ambient temperature (Figure 2, bottom).…”
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