2022
DOI: 10.1039/d1sc06719b
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Dimerizing cascades of enallenamides reveal the visible-light-promoted activation of cumulated C–C double bonds

Abstract: The visible-light-promoted activation of conjugated C-C double bonds is well developed while that of cumulated systems is underexplored. We present the feasibility of this challenging approach. The localization of a...

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Cited by 16 publications
(16 citation statements)
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“…In some molecular systems containing a large conjugated πbond structure with a rigid planar structure, photon energy could induce conformational changes near the conjugated double bonds, 96 which could lead to an overall shift of the molecular principal axes from a planar to a three-dimensional structure. This phenomenon is also the origin of the spatial siteblocking effect of some organic small molecules in response to light stimulation.…”
Section: Operational Mechanisms Of Azobenzene Derivatives and Their P...mentioning
confidence: 99%
“…In some molecular systems containing a large conjugated πbond structure with a rigid planar structure, photon energy could induce conformational changes near the conjugated double bonds, 96 which could lead to an overall shift of the molecular principal axes from a planar to a three-dimensional structure. This phenomenon is also the origin of the spatial siteblocking effect of some organic small molecules in response to light stimulation.…”
Section: Operational Mechanisms Of Azobenzene Derivatives and Their P...mentioning
confidence: 99%
“…The method involves a sequential C(sp 3 )-O bond cleavage/C(sp 3 )-H bond functionalization, which is an original reactivity in the field of Ag-promoted processes. [17][18][19][20] As part of an ongoing interest on synthetic cascades, [21][22][23][24][25] we serendipitously observed the formation of macrocycle 2 in the presence of a Ru-based catalytic system originally developed by Sato and Mori 26 while treating diendiyne 1 with an Ag (I) salt. We soon realized that the Ag(I) salt used to trigger a putative chloride abstraction was actually the competent species for the conversion of 1 into 2.…”
mentioning
confidence: 98%
“…As part of an ongoing interest on synthetic cascades, 21–25 we serendipitously observed the formation of macrocycle 2 in the presence of a Ru-based catalytic system originally developed by Sato and Mori 26 while treating diendiyne 1 with an Ag( i ) salt. We soon realized that the Ag( i ) salt used to trigger a putative chloride abstraction was actually the competent species for the conversion of 1 into 2 .…”
mentioning
confidence: 99%
“…As part of an ongoing interest in atom-economical cascades, we recently reported a MnO 2 -promoted sequence that converts styrylynols into tricyclic naphthalenes . Substrates were prepared by treating a 1,6-enyne with butyl lithium and quenching the so-formed carbanion with an acyl chloride.…”
mentioning
confidence: 99%
“…DFT modeling was carried out at the M06/Def2-TZVP level, using THF and MeCN as implicit solvents. We considered 15 different reactions that convert I (or III ) into the corresponding cyclized species II (or IV ), varying the tether, the propargylic substituent, and the presence of alkali cations (see the SI for the complete set of data).…”
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confidence: 99%