Rhodium‐Catalyzed Cyclization Reaction of 1,6‐Enynes with Arylboronic Acids through β‐Hydride Elimination/Hydrorhodation Sequence | Zendy

Shimada Masahiko | Zendy; Harumashi Tatsuro | Zendy; Miura Tomoya | Zendy; Murakami Masahiro | Zendy

Premium

Rhodium‐Catalyzed Cyclization Reaction of 1,6‐Enynes with Arylboronic Acids through β‐Hydride Elimination/Hydrorhodation Sequence

Author(s) -

Shimada Masahiko,

Harumashi Tatsuro,

Miura Tomoya,

Murakami Masahiro

Publication year - 2008

Publication title -

chemistry – an asian journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.18

H-Index - 106

eISSN - 1861-471X

pISSN - 1861-4728

DOI - 10.1002/asia.200700407

Subject(s) - rhodium , transmetalation , chemistry , intramolecular force , hydride , medicinal chemistry , catalysis , sequence (biology) , boron , elimination reaction , intermolecular force , combinatorial chemistry , organic chemistry , molecule , hydrogen , biochemistry

Methoxy‐substituted 1,6‐enynes react with arylboronic acids in the presence of a rhodium(I) complex to give arylated cyclization products. This occurs by a multi‐step mechanism consisting of rhodium/boron transmetalation, intermolecular carborhodation, intramolecular carborhodation, β‐hydride elimination, hydrorhodation, and β‐oxygen elimination. A shift of the position of a carbon–carbon double bond is observed, suggesting that the β‐hydride elimination/hydrorhodation process is repeatedly taking place.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research