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2 article(s) from Boaz, Nicholas C

A new synthesis of Tyrian purple (6,6’-dibromoindigo) and its corresponding sulfonate salts

Holly Helmers,
Mark Horton,
Julie Concepcion,
Jeffrey Bjorklund and
Nicholas C. Boaz

Beilstein J. Org. Chem. 2026, 22, 167–174, doi:10.3762/bjoc.22.10

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Scheme 1: A) Generalized synthetic scheme for several previous syntheses of 6,6’-dibromoindigo. B) The synthe...

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Scheme 2: Synthetic scheme for the preparation of 6,6’-dibromoindigo from p-bromotoluene (5).

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Scheme 3: Nitration of p-bromotoluene (5) yields a mixture of regioisomers 3 and 7.

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Scheme 4: Benzylic bromination of 4-bromo-2-nitrotoluene (3).

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Scheme 5: A) Treatment of 4-bromo-2-nitrobenzyl bromide (6) with DMSO did not yield the alkoxysulfonium ion i...

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Scheme 6: Condensation of 4-bromo-2-nitrobenzaldehyde (4) to yield 6,6’-dibromoindigo (1).

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Scheme 7: A) Disulfonation of 6,6’-dibromoindigo (1), to yield 6,6’-dibromo-5,5’-indigodisulfonic acid disodi...

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Figure 1: A) UV–vis spectra of 6,6’-dibromo-5,5’,7-indigotrisulfonic acid trisodium salt (10) (10 μM) in aque...

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Published 21 Jan 2026

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Selective benzylic C–H monooxygenation mediated by iodine oxides

Kelsey B. LaMartina,
Haley K. Kuck,
Linda S. Oglesbee,
Asma Al-Odaini and
Nicholas C. Boaz

Beilstein J. Org. Chem. 2019, 15, 602–609, doi:10.3762/bjoc.15.55

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Figure 1: Catalyst optimization for the monooxidation of n-butylbenzene mediated by the iodate anion.

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Figure 2: NHPI-catalyzed oxidation of secondary benzylic C–H bonds mediated by iodine(V). ^a100 °C for 18 h; ^b...

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Figure 3: NHPI-catalyzed oxidation of di-benzylic C–H bonds mediated by iodate.

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Figure 4: NHPI-catalyzed oxidation of substrates containing primary and tertiary benzylic C–H bonds. ^aReactio...

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Figure 5: Competitive deuterium KIE for the oxidation of ethyl benzene by the NHPI-iodate system.

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Figure 6: Pyrolysis of an acyl perester in the presence of molecular iodine.

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Figure 7: Proposed mechanism for the selective monooxygenation of benzylic C–H bonds.

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Published 05 Mar 2019

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