Reported is the first example of a rhodium‐mediated β‐sulfide elimination, which represents a new mode of reactivity for late‐transition‐metal chemistry. This serendipitous discovery facilitates an ene‐cycloisomerization of allylic‐sulf...
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https://www.riss.kr/link?id=O120448801
2018년
-
1433-7851
1521-3773
SCI;SCIE;SCOPUS
학술저널
673-677 [※수록면이 p5 이하이면, Review, Columns, Editor's Note, Abstract 등일 경우가 있습니다.]
0
상세조회0
다운로드다국어 초록 (Multilingual Abstract)
Reported is the first example of a rhodium‐mediated β‐sulfide elimination, which represents a new mode of reactivity for late‐transition‐metal chemistry. This serendipitous discovery facilitates an ene‐cycloisomerization of allylic‐sulf...
Reported is the first example of a rhodium‐mediated β‐sulfide elimination, which represents a new mode of reactivity for late‐transition‐metal chemistry. This serendipitous discovery facilitates an ene‐cycloisomerization of allylic‐sulfide‐containing alkenylidenecyclopropanes (ACPs) to afford five‐membered carbo‐ and heterocyclic rings with concomitant intramolecular thioether migration. Interestingly, similar selectivity is obtained with both E‐ and Z‐allylic sulfides and the reaction is also feasible with an allylic selenide. Mechanistic studies are consistent with an inner‐sphere transfer of the sulfide, which is remarkable given the propensity for sulfides to poison transition‐metal catalysts. Finally, this type of atom‐economical rearrangement is envisioned to prompt the development of related processes given the utility of sulfides in target‐directed synthesis.
À la mode: Reported is the first example of a rhodium‐mediated β‐sulfide elimination. The reaction represents a new mode of reactivity for late‐transition‐metal chemistry. Rhodium facilitates an ene‐cycloisomerization of allylic‐sulfide‐containing alkenylidenecyclopropanes (ACPs) to give five‐membered carbo‐ and heterocyclic rings with concomitant intramolecular thioether migration. COD=1,5‐cyclooctadiene, Ts=4‐toluenesulfonyl.
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