Open AccessTwo-Carbon Ring Expansion of 1-Indanones via Insertion of Ethylene into Carbon–Carbon Bonds
Author(s) -
Ying Xia,
Shusuke Ochi,
Guangbin Dong
Publication year - 2019
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.9b07445
Subject(s) - chemistry , ethylene , ring (chemistry) , carbon fibers , rhodium , molecule , reinforced carbon–carbon , catalysis , combinatorial chemistry , organic chemistry , materials science , composite number , composite material
A rhodium-catalyzed direct insertion of ethylene into a relatively unstrained carbon-carbon bond in 1-indanones is reported, which provides a two-carbon ring expansion strategy for preparing seven-membered cyclic ketones. As many 1-indanones are commercially available and ethylene is inexpensive, this strategy simplifies synthesis of benzocycloheptenones that are valuable synthetic intermediates for bioactive compounds but challenging to prepare otherwise. In addition, the reaction is byproduct-free, redox neutral, and tolerant of a wide range of functional groups, which may have implications on unconventional strategic bond disconnections for preparing complex cyclic molecules.