2018
DOI: 10.3762/bjoc.14.96
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Iodine(III)-mediated halogenations of acyclic monoterpenoids

Abstract: Five different halofunctionalizations of acyclic monoterpenoids were performed using a combination of a hypervalent iodine(III) reagent and a halide salt. In this manner, the dibromination, the bromo(trifluoro)acetoxylation, the bromohydroxylation, the iodo(trifluoro)acetoxylation or the ene-type chlorination of the distal trisubstituted double bond occurred with excellent selectivity and moderate to good yields.

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Cited by 11 publications
(9 citation statements)
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“…In order to broaden the range of substrates that could be attainable by a direct cyclization, we wished to develop a reaction following a specific blueprint: avoiding the use of transition metals, no heating and installing a linchpin for further derivatizations. Based on our previous studies on hypervalent iodine(III) [19][20][21][22][23][24] -mediated halogenations, [25][26][27][28] and in particular modular halocyclizations, [29,30] we chose to focus on the bromocyclization of unsaturated N-oxyureas (5, Scheme 2). These substrates are challenging in terms of regio-and chemo-selectivity.…”
Section: Reaction Designmentioning
confidence: 99%
“…In order to broaden the range of substrates that could be attainable by a direct cyclization, we wished to develop a reaction following a specific blueprint: avoiding the use of transition metals, no heating and installing a linchpin for further derivatizations. Based on our previous studies on hypervalent iodine(III) [19][20][21][22][23][24] -mediated halogenations, [25][26][27][28] and in particular modular halocyclizations, [29,30] we chose to focus on the bromocyclization of unsaturated N-oxyureas (5, Scheme 2). These substrates are challenging in terms of regio-and chemo-selectivity.…”
Section: Reaction Designmentioning
confidence: 99%
“…We attempted to prepare the ammonium‐complexed halogen(I) species following the procedure reported by Toth, [10a] but a UV‐absorbing yellow solid was obtained; its structure is proposed to be 16 or its polymer (Figure 3A) based on NMR spectroscopy, HRMS, and its ability to chlorinate a monoterpenoid [10o] (Figure 3B) and indole (Figure 3C, left). When PIFA and n ‐Bu 4 NCl ⋅ H 2 O were replaced with 16 , oxindole product 11 a was produced in 73% yield under otherwise standard conditions (Figure 3C, right).…”
Section: Resultsmentioning
confidence: 99%
“…Lastly, Cariou and coworkers recently demonstrated a chemodivergent, tunable, and selective method for bromofunctionalization of polyprenoids (Scheme 34) [107,108]. Depending on the combination of a hypervalent iodine source, inorganic salt, solvent, and temperature, the reaction produced selective dibromination, oxy-bromination, and bromocyclization reactions.…”
Section: Alkene Dihalogenationmentioning
confidence: 99%