2020-02-24 08:47:24
Coralie Duchemin and Nicolai Cramer
Hydroxylamine derivatives are not only important motifs in pharmaceuticals and agrochemicals but as well valuable sub- strates for a variety of complexity-building transformations. For instance, hydroxylamine derivatives have been extensively used as directing groups in catalytic C–H functionalizations and concomitant cleavage of the oxygen–nitrogen bond allowed reoxidation of the catalyst (Scheme 1).3 In this context, phenoxyamides were established as efficient internal oxidants for Rh(III)-catalyzed aryl C(sp2)–H functionalizations.4 Rovis disclosed related Rh(III)-catalyzed vinylic C(sp2)–H functionali- zations using the related enoxyphthalimide motif as the oxi- dative directing group.5 Subsequent trapping reactions with Michael acceptors were used to selectively form trans-5a or cis- cyclopropanes,5c as well as to trigger carboaminations5b Moreover, the ability of oxyamides to engage in radical pro- cesses has been exploited in the decarboxylative functionali- zation of redox active esters triggered either photocatalytically6 or by nickel complexes.7 Along the same lines, Feng reported a photo-catalyzed process for the carboamination of alkenes with N-enoxyphthalimides.8
Despite this steeply increasing synthetic versatility, efficient access to the N-enoxyimide structural motif is still very cum- bersome and represents an unsolved problem. Except for the direct Michael-addition of N-hydroxyimides to acetylene dicar- boxylates,9 the only general reported route involves preparation of the vinylboronic acid in three steps from the corresponding alkene (Scheme 2).5a In turn, the vinylboronic acid is subjected to a copper(I)-mediated coupling with N-hydroxyphthalimide.10 Besides the drawbacks of the low synthetic efficiency of a three-step procedure and the use of copper-mediated reac- tions, this protocol is only suited for N-hydroxy-phthalimides. Related substrates like N-hydroxysuccinimide or N-hydroxy- carbamate do not engage in the transformation.10b
Gold(I)-catalyzed additions of oxygen nucleophiles to term- inal alkynes have become an efficient method for the synthesis of a variety of O-vinyl derivatives.11 For instance, the addition of HOBt to alkynes was reported by Hammond and Xu.12 Zhang disclosed the synthesis of indoles by the addition of aryl hydroxamic acids and N-aryl-N-hydroxycarbamates to alkynes forming labile vinyl ether intermediates which readily rearranged in analogy to the Fischer indole synthesis.13 Moreover, the addition of pyridine N-oxides to alkynes is used for enolate umpolung reactivities.14 Notably, hydroxylamine deriva- tives with two electron-withdrawing substituents on the nitrogen atom such as N-hydroxylimides have not been investigated as suitable nucleophiles. Given the need for an efficient synthetic access and inspired by these reports, we explored the feasibility of a gold(I)-catalyzed efficient single step synthesis of N-enoxy- imides by the addition of N-hydroxyimides to widely accessible terminal alkynes (Scheme 2).
To initially investigate the transformation, we selected 4-methoxyphenyl acetylene (1a) and N-hydroxysuccinimide 2a as the model substrates. The envisioned addition of 1a to the acetylene was accomplished by (PPh3)Au trifluoroacetate in DCE at 90 °C for 6 h. By in situ generation of the gold catalyst, the desired addition product 3aa was obtained in 26% yield (Table 1, entry 1). The yield of 3aa was substantially increased to 65% with a preformed (PPh3)Au trifluoroacetate catalyst (entry 2). The observation points towards decomposition of formed product 3aa under the reaction conditions. Conducting the reaction under strictly anhydrous conditions had no effect on the amount of 4a (entry 3). A five-fold scale- up of the reaction increased the isolated yield of product 3aa to 75% (entry 4). The moderate stability of 3aa which has the tendency to decompose under the reaction conditions to ketone 4a requires striking a fine balance to maximize yield. The reaction outcome proved to be as well highly sensitive to several variables. Notably, replacing the trifluoroacetate anion by weaker coordinating ones such as triflate or triflimide15 was to be detrimental (entries 5 and 6). In these cases, a formal hydration of 1a was dominant yielding exclusively ketone 4a. Subsequent variations of the ligand (IPr or Johnphos) did not substantially improve the reaction outcome (entries 7 and 8).16 Longer reaction times caused a reduction of 3aa and increased the ketone 4a (entry 9), whereas lower reaction temperatures (60 °C) or lower concentrations gave largely reduced conver- sions (entries 10 and 11). Attempts to increase the formation of 3aa by increasing the equivalents of N-hydroxysuccinimide failed (entry 12). Several control experiments were conducted to gauge the relevance of the individual components of the catalyst system. In this respect, the absence of the gold catalyst completely shut down the formation of addition product 3aa (entry 13), which excluded residual Ag(I) salts as the active cata- lyst.17 Omitting the addition of silver salts completely showed that neutral (PPh3)AuCl is not a competent catalyst and caused only unspecific degradation of 1a (entry 14). These experi- ments underlined the relevance of the trifluoroacetate anion in gold(I)-catalyzed transformations to modulate reactivity and selectivity.18,19 Moreover, trifluoroacetic acid itself did not promote the addition of succinimide at all (entry 15).
Next, the scope of the reaction was investigated with opti- mized conditions (Scheme 3). The electronic nature of the aryl substituent of the alkyne was found to have an influence on the reactivity. The reaction works best with alkynes having electron-rich aryl groups and was somewhat less efficient for those with electron-deficient aryl or sterically hindered substi- tuents. Nevertheless, the obtained yield of the single step transformation is still largely competitive with the reported 4-step sequence which is not described for N-hydroxysuccinimdes. Pleasingly, alkenyl- and alkyl-substi- tuted alkynes are particularly well suited for the gold-catalysed addition.
To briefly illustrate the utility of the transformation and the synthetic potential of the enoxyimides, 3ba was used as the substrate in two very recently reported state-of-the-art catalytic transformations. For instance, exposure of N-enoxysuccinimide 3ba to conditions reported by Rovis,5a [Cp*RhCl2]2 in the presence of cesium acetate and ethyl acryl- ate, provided cyclopropane 5 in 72% yield in 61 : 39 cis/trans ratio (Scheme 4). The switch from the original phthalimide group to the succinimide group resulted in a substrate induced cis-dominance. A catalyst-induced cis-selectivity could be obtained for enoxyphthalimide by fine-tuning of the cata- lyst.5c Combined with catalyst engineering, the outlined succi- nimide-type substrate might become useful to boost cis-selecti- vity for refractory substrates or to serve as a suitable platform to develop catalytic enantioselective cyclopropanation reac- tions with chiral cyclopentadienyl complexes.20 Moreover, N-enoxysuccinimide 3ba successfully participated in an iridium-photo-catalyzed carboamination of olefins in analogy to recently disclosed work by Feng.8 For instance, irradiation of a mixture of 3ba ethylvinylether in the presence of an iridium photocatalyst triggered smooth carboamination and formed ketone 6 in 52% yield. To the best of our knowledge, this represents a rare example of an N-oxysuccinimide moiety in a visible light photoinduced radical process.21
Conclusion
In summary, we reported a gold(I)-catalyzed addition of N-hydroxyimides to terminal alkynes. Formal alkyne hydration presumably by decomposition of the desired N-enoxyimide product was mitigated by using a trifluoroacetate counterion on the gold(I) complex. The process accommodates several N-hydroxyimides and a range of aryl, alkenyl and alkyl alkynes decorated with a variety of functional groups including halo- gens, phthalimides, esters and ethers. N-Enoxysuccinimides were shown to be suitable substrates for Rh(III)-catalyzed cyclo- propanations and photo-redox carboaminations. We expect that the reported efficient N-enoxyimide preparation will further enable exploitation of their untapped synthetic potential.
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DimethomorphCatalog No.:AA00HBNL CAS No.:110488-70-5 MDL No.:MFCD01632781 MF:C21H22ClNO4 MW:387.8567 |
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N'-(5,7-Dimethyl-1,3-benzothiazol-2-yl)-N,N-diethylethane-1,2-diamineCatalog No.:AA01ARLG CAS No.:1105188-31-5 MDL No.:MFCD11986994 MF:C15H23N3S MW:277.4282 |
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4-Methyl-n-(3-morpholin-4-ylpropyl)-1,3-benzothiazol-2-amineCatalog No.:AA01ARN3 CAS No.:1105188-50-8 MDL No.:MFCD11987004 MF:C15H21N3OS MW:291.4117 |
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4-Fluoro-N-(3-morpholin-4-ylpropyl)-1,3-benzothiazol-2-amineCatalog No.:AA01ARN4 CAS No.:1105188-56-4 MDL No.:MFCD11987006 MF:C14H18FN3OS MW:295.3756 |
5-Methoxy-N-(3-morpholinopropyl)benzo[d]thiazol-2-amineCatalog No.:AA01FME2 CAS No.:1105188-59-7 MDL No.:MFCD11987007 MF:C15H21N3O2S MW:307.4111 |
6-Methyl-N-(3-morpholin-4-ylpropyl)-1,3-benzothiazol-2-amineCatalog No.:AA01ARNU CAS No.:1105188-63-3 MDL No.:MFCD11987008 MF:C15H21N3OS MW:291.4117 |
6-Methoxy-N-(3-morpholinopropyl)benzo[d]thiazol-2-amineCatalog No.:AA01FMDV CAS No.:1105188-66-6 MDL No.:MFCD11987009 MF:C15H21N3O2S MW:307.4111 |
6-Fluoro-N-(3-morpholin-4-ylpropyl)-1,3-benzothiazol-2-amineCatalog No.:AA01ARNV CAS No.:1105188-69-9 MDL No.:MFCD11987010 MF:C14H18FN3OS MW:295.3756 |
4,6-Difluoro-N-(3-morpholinopropyl)benzo[d]thiazol-2-amineCatalog No.:AA01FMDQ CAS No.:1105188-72-4 MDL No.:MFCD11987011 MF:C14H17F2N3OS MW:313.3661 |
4,7-Dimethoxy-N-(3-morpholinopropyl)benzo[d]thiazol-2-amineCatalog No.:AA01FME1 CAS No.:1105188-79-1 MDL No.:MFCD11987013 MF:C16H23N3O3S MW:337.4371 |
7-Chloro-4-methyl-N-(3-morpholinopropyl)benzo[d]thiazol-2-amineCatalog No.:AA01FMDF CAS No.:1105188-86-0 MDL No.:MFCD11987015 MF:C15H20ClN3OS MW:325.8568 |
N'-(7-CHLORO-4-METHOXY-1,3-BENZOTHIAZOL-2-YL)-N,N-DIMETHYLETHANE-1,2-DIAM+Catalog No.:AA01AROO CAS No.:1105188-90-6 MDL No.:MFCD11987016 MF:C12H16ClN3OS MW:285.7929 |
N'-(7-CHLORO-4-METHOXY-1,3-BENZOTHIAZOL-2-YL)-N,N-DIMETHYLPROPANE-1,3-DIA+Catalog No.:AA01AROP CAS No.:1105188-94-0 MDL No.:MFCD11987017 MF:C13H18ClN3OS MW:299.8195 |
7-Chloro-4-methoxy-N-(3-morpholinopropyl)benzo[d]thiazol-2-amineCatalog No.:AA01FME0 CAS No.:1105188-98-4 MDL No.:MFCD31731182 MF:C15H20ClN3O2S MW:341.8562 |
N'-(7-CHLORO-4-METHOXY-1,3-BENZOTHIAZOL-2-YL)-N,N-DIETHYLETHANE-1,2-DIAMI+Catalog No.:AA01AS8X CAS No.:1105189-02-3 MDL No.:MFCD11987019 MF:C14H20ClN3OS MW:313.8461 |
7-Chloro-4-methoxy-N-(2-morpholinoethyl)benzo[d]thiazol-2-amineCatalog No.:AA01FME5 CAS No.:1105189-05-6 MDL No.:MFCD11987020 MF:C14H18ClN3O2S MW:327.8296 |
4-Methyl-n-(2-morpholin-4-ylethyl)-1,3-benzothiazol-2-amineCatalog No.:AA01FME6 CAS No.:1105189-08-9 MDL No.:MFCD11987021 MF:C14H19N3OS MW:277.3852 |
4-Fluoro-N-(2-morpholin-4-ylethyl)-1,3-benzothiazol-2-amineCatalog No.:AA01ARPM CAS No.:1105189-11-4 MDL No.:MFCD11987022 MF:C13H16FN3OS MW:281.3490 |
5-Methoxy-N-(2-morpholin-4-ylethyl)-1,3-benzothiazol-2-amineCatalog No.:AA01ARPN CAS No.:1105189-14-7 MDL No.:MFCD11987023 MF:C14H19N3O2S MW:293.3846 |
6-Methoxy-N-(2-morpholin-4-ylethyl)-1,3-benzothiazol-2-amineCatalog No.:AA01ARPP CAS No.:1105189-20-5 MDL No.:MFCD11987025 MF:C14H19N3O2S MW:293.3846 |
6-Chloro-N-(2-morpholin-4-ylethyl)-1,3-benzothiazol-2-amineCatalog No.:AA01ARPQ CAS No.:1105189-23-8 MDL No.:MFCD11987026 MF:C13H16ClN3OS MW:297.8036 |
6-Fluoro-N-(2-morpholin-4-ylethyl)-1,3-benzothiazol-2-amineCatalog No.:AA01ARQF CAS No.:1105189-26-1 MDL No.:MFCD11987027 MF:C13H16FN3OS MW:281.3490 |
4,6-Difluoro-N-(2-morpholin-4-ylethyl)-1,3-benzothiazol-2-amineCatalog No.:AA01ARQG CAS No.:1105189-32-9 MDL No.:MFCD11987029 MF:C13H15F2N3OS MW:299.3395 |
5,7-Dimethyl-N-(2-morpholin-4-ylethyl)-1,3-benzothiazol-2-amineCatalog No.:AA01ARQH CAS No.:1105189-35-2 MDL No.:MFCD11987030 MF:C15H21N3OS MW:291.4117 |
5-Ethyl-3-mercapto[1,2,4]triazolo[4,3-(a)]pyrimidin-7(8(h))-oneCatalog No.:AA01ARP8 CAS No.:1105189-36-3 MDL No.:MFCD11986381 MF:C7H8N4OS MW:196.2296 |
4,7-Dimethoxy-N-(2-morpholinoethyl)benzo[d]thiazol-2-amineCatalog No.:AA01FME4 CAS No.:1105189-39-6 MDL No.:MFCD11987031 MF:C15H21N3O3S MW:323.4105 |
3-MERCAPTO-5-PROPYL[1,2,4]TRIAZOLO[4,3-(A)]PYRIMIDIN-7(8(H))-ONECatalog No.:AA01ARP9 CAS No.:1105189-40-9 MDL No.:MFCD11986382 MF:C8H10N4OS MW:210.2562 |
7-Chloro-4-methyl-N-(2-morpholinoethyl)benzo[d]thiazol-2-amineCatalog No.:AA01FMDS CAS No.:1105189-47-6 MDL No.:MFCD11987033 MF:C14H18ClN3OS MW:311.8302 |
5-Amino-1-tert-butyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-oneCatalog No.:AA01ARPX CAS No.:1105189-48-7 MDL No.:MFCD11986385 MF:C9H13N5O MW:207.2324 |
2-chloro-4-methanesulfonyl-1,3-benzothiazoleCatalog No.:AA01ARR5 CAS No.:1105189-51-2 MDL No.:MFCD11987034 MF:C8H6ClNO2S2 MW:247.7217 |
5-Amino-1-(4-methylphenyl)-1,5-dihydro-4h-pyrazolo[3,4-d]pyrimidin-4-oneCatalog No.:AA01ARPY CAS No.:1105189-52-3 MDL No.:MFCD11986386 MF:C12H11N5O MW:241.2486 |
7-Chloro-n-(2-furylmethyl)-4-methoxy-1,3-benzothiazol-2-amineCatalog No.:AA01ARRW CAS No.:1105189-55-6 MDL No.:MFCD11987036 MF:C13H11ClN2O2S MW:294.7566 |
5-AMINO-1-(3,4-DIMETHYLPHENYL)-1,5-DIHYDRO-4H-PYRAZOLO[3,4-D]PYRIMIDIN-4-+Catalog No.:AA01ARPZ CAS No.:1105189-56-7 MDL No.:MFCD11986387 MF:C13H13N5O MW:255.2752 |
6-Nitro-N-(pyridin-2-ylmethyl)-1,3-benzothiazol-2-amineCatalog No.:AA01ARRX CAS No.:1105189-59-0 MDL No.:MFCD11987037 MF:C13H10N4O2S MW:286.3091 |
2-(4-Phenylpiperazin-1-yl)benzo[d]thiazol-6-olCatalog No.:AA01FMMG CAS No.:1105189-63-6 MDL No.:MFCD11987040 MF:C17H17N3OS MW:311.4014 |
2-(4-Ethylpiperazin-1-yl)-1,3-benzothiazol-6-olCatalog No.:AA01ARSO CAS No.:1105189-67-0 MDL No.:MFCD11987042 MF:C13H17N3OS MW:263.3586 |
3-[5-(furan-2-yl)-1,3,4-oxadiazol-2-yl]piperidineCatalog No.:AA01ARIJ CAS No.:1105189-75-0 MDL No.:MFCD11937169 MF:C11H13N3O2 MW:219.2398 |
Ethyl (3-amino-4H-thieno[3,4-c]pyrazol-2(6H)-yl)acetateCatalog No.:AA01ARL0 CAS No.:1105190-33-7 MDL No.:MFCD11986669 MF:C9H13N3O2S MW:227.2834 |
1-Isobutyl-5-(4-methoxyphenyl)-1,3-dihydro-2H-imidazole-2-thioneCatalog No.:AA01AQLT CAS No.:1105190-34-8 MDL No.:MFCD16653449 MF:C14H18N2OS MW:262.3705 |
3,6-dimethyl-2-sulfanyl-3H,4H,6H,7H-thieno[3,2-d]pyrimidin-4-oneCatalog No.:AA019TKK CAS No.:1105190-40-6 MDL No.:MFCD11986411 MF:C8H10N2OS2 MW:214.3078 |
2-Chloro-3-isopropoxypyridineCatalog No.:AA00HBNS CAS No.:1105190-61-1 MDL No.:MFCD16653100 MF:C8H10ClNO MW:171.6241 |
(5-Oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidin-3-yl)acetic acidCatalog No.:AA01ARHL CAS No.:1105190-66-6 MDL No.:MFCD11518875 MF:C8H8N2O3S MW:212.2257 |
2-Chloro-3-[(2-fluorobenzyl)oxy]pyridineCatalog No.:AA01ARMZ CAS No.:1105190-67-7 MDL No.:MFCD11986848 MF:C12H9ClFNO MW:237.6574 |
