2018
DOI: 10.1515/pac-2017-0414
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Molecular iodine as a mild catalyst for cross-coupling of alkenes and alcohols

Abstract: C-C bond formation is one of the most fundamental approaches toward molecular diversity in organic synthesis. In pursuit of environmentally friendlier chemical approaches to organic chemistry, we present a new metal-free method for direct dehydrative cross-coupling of alcohols and alkenes using molecular iodine as a Lewis acid catalyst under solvent-free reaction conditions. The reaction is atom-economical, tolerant to air and allows simple synthetic procedure, furnishing C sp 3 -C sp 2 coupling products with … Show more

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Cited by 19 publications
(14 citation statements)
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“…In the presence of protic solvents, iodine is known to decompose slowly to form Brønsted acid HI, which is responsible for further reaction catalysis. 21 However, from the observations of Table 1, no reaction proceeded at all in protic solvents such as H 2 O, MeOH, and EtOH (Table 1, entries 14–16), which clearly rules out the contribution of Brønsted acid mode of catalysis by molecular iodine. On the other hand, iodine in most aprotic solvents gave acceptable yields (Table 1, entries 1 and 9–11), which accounts for the halogen-bond activation mechanism of molecular iodine.…”
Section: Resultsmentioning
confidence: 92%
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“…In the presence of protic solvents, iodine is known to decompose slowly to form Brønsted acid HI, which is responsible for further reaction catalysis. 21 However, from the observations of Table 1, no reaction proceeded at all in protic solvents such as H 2 O, MeOH, and EtOH (Table 1, entries 14–16), which clearly rules out the contribution of Brønsted acid mode of catalysis by molecular iodine. On the other hand, iodine in most aprotic solvents gave acceptable yields (Table 1, entries 1 and 9–11), which accounts for the halogen-bond activation mechanism of molecular iodine.…”
Section: Resultsmentioning
confidence: 92%
“…On the other hand, iodine in most aprotic solvents gave acceptable yields (Table 1, entries 1 and 9–11), which accounts for the halogen-bond activation mechanism of molecular iodine. 21 It also explains why no product formation was observed in DMSO and DMF despite being aprotic solvents as they are expected to form strong halogen bonds with molecular iodine resulting in deactivation of the catalyst for further reaction. 21 The reaction did not require any external base or additives.…”
Section: Resultsmentioning
confidence: 99%
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“…Our previous work described a convenient esterification method mediated by N -bromosuccinimide in substoichiometric amounts for direct esterification [42]. With this in mind, and in the context of our continued interest in improving and developing environmentally acceptable synthetic protocols [43,44,45,46,47,48], we now report the precatalytic activity of easily manipulable, metal-free DBDMH in the direct esterification of carboxylic acids and alcohols and in the aldol condensation of aldehydes.…”
Section: Introductionmentioning
confidence: 97%
“…[16] For instance, in 2018, Stavber and coworkers presented a metalfree method for direct cross-coupling of alcohols and alkenes using iodine as Lewis acid with 9 examples. [17] Gu's group demonstrated the combination of Lewis acids and Lewis bases was effective for the alkenes synthesis via alcohol dehydration in 2016. [18] To the best of our knowledge, no examples in which fluorenols were employed for the coupling with diarylethylene has been explored.…”
Section: Introductionmentioning
confidence: 99%