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Synthesis of Alkynylmethylidene-benzoxasiloles through a Rhodium-Catalyzed Cycloisomerization Involving 1,2-Silicon and 1,3-Carbon Migration.
Namba, Tomoya; Kawauchi, Susumu; Shibata, Yu; Kanno, Hiroshi; Tanaka, Ken.
Affiliation
  • Namba T; Department of Chemical Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550, Japan.
  • Kawauchi S; Department of Chemical Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550, Japan.
  • Shibata Y; Department of Chemical Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550, Japan.
  • Kanno H; Department of Chemical Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550, Japan.
  • Tanaka K; Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184-8588, Japan.
Angew Chem Int Ed Engl ; 56(11): 3004-3008, 2017 03 06.
Article in En | MEDLINE | ID: mdl-28157262
ABSTRACT
It is shown that a cationic rhodium(I)/biphep complex catalyzes the cycloisomerization of 2-(alkynylsilylethynyl)phenols, leading to alkynylmethylidene-benzoxasiloles through concomitant silicon and carbon migration. This unprecedented cycloisomerization presumably proceeds via the formation of rhodium vinylidenes through 1,2-silicon migration, followed by 1,3-carbon (alkyne) migration via the formation of hypervalent silicon centers.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Angew Chem Int Ed Engl Year: 2017 Document type: Article
Fulltext
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PubMed Links
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Angew Chem Int Ed Engl Year: 2017 Document type: Article