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. 2014 May 23:10:1220-1227.
doi: 10.3762/bjoc.10.120. eCollection 2014.

Synthesis of ethoxy dibenzooxaphosphorin oxides through palladium-catalyzed C(sp(2))-H activation/C-O formation

Seohyun Shin #  1   2 , Dongjin Kang #  1   2 , Woo Hyung Jeon  1   2 , Phil Ho Lee  1   2
Affiliations

Synthesis of ethoxy dibenzooxaphosphorin oxides through palladium-catalyzed C(sp(2))-H activation/C-O formation

Seohyun Shin et al. Beilstein J Org Chem. .

Abstract

We report an efficient Pd-catalyzed C(sp(2))-H activation/C-O bond formation for the synthesis of ethoxy dibenzooxaphosphorin oxides from 2-(aryl)arylphosphonic acid monoethyl esters under aerobic conditions.

Keywords: C–H activation; catalysis; cyclization; palladium; phosphorus heterocyclic compound.

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Figures

Scheme 1
Scheme 1
Synthesis of alkoxy dibenzooxaphosphorin oxides by C(sp2)–H activation/C–O formation.
Scheme 2
Scheme 2
Preparation of 2-(aryl)arylphosphonic acid monoethyl esters.
Scheme 3
Scheme 3
A variety of organic acids and monoprotected amino acids as ligands.
Scheme 4
Scheme 4
Cyclization of 2-arylphenylphosphonic acid monoethyl esters.
Scheme 5
Scheme 5
Cyclization of 2-(aryl)arylphosphonic acid monoethyl esters.
Scheme 6
Scheme 6
Preparation of 1a-[D5].
Scheme 7
Scheme 7
Preparation of 1a-[D1].
Scheme 8
Scheme 8
Studies with isotopically labelled compounds.
Scheme 9
Scheme 9
A plausible mechanism.
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