Substitution controlled functionalization of ortho -bromobenzylic alcohols via palladium catalysis: Synthesis of chromenes and indenols

Mahendar, L and G, Satyanarayana (2014) Substitution controlled functionalization of ortho -bromobenzylic alcohols via palladium catalysis: Synthesis of chromenes and indenols. Journal of Organic Chemistry, 79 (5). pp. 2059-2074. ISSN 0022-3263

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Abstract

An efficient domino Pd-catalyzed transformation of simple ortho-bromobenzyl tertiary alcohols to chromenes is presented. Their formation is believed to proceed via the formation of a five-membered palladacycle, which, in turn, involves in an intermolecular homocoupling with the second ortho- bromobenzyltertiary alcohol to yield the homo-biaryl bond followed by intramolecular C-O bond formation. Interestingly, when there is an allylic substituent on the benzylic carbon atom, a chemoselective switch was observed, which preferred intramolecular Heck coupling and gave indenols. Further, it has been confirmed that the tertiary alcohol functionality is indispensible to give the coupled products, whereas the use of primary/secondary benzylic alcohols furnished the simple carbonyl products via a possible reductive debromination followed by oxidation due to the availability of β-hydrogen(s) - [Any research collaboration contact author at gvsatya[at]iith[dot]ac[dot]in]

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IITH Creators:

IITH Creators	ORCiD
G, Satyanarayana	UNSPECIFIED

Item Type:

Article

Uncontrolled Keywords:

Benzylic alcohols; Benzylic carbon; C-O bond formation; Carbonyl products; Functionalizations; Palladium catalysis; Reductive debromination; Tertiary alcohols

Subjects:

?? sub5.8 ??

Divisions:

Department of Chemistry

Depositing User:

Team Library

Date Deposited:

24 Dec 2014 10:44

Last Modified:

24 Sep 2015 10:06

URI:

http://raiithold.iith.ac.in/id/eprint/1242