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Strain-promoted oxidative annulation of arynes and cyclooctynes with benzamides: palladium-catalyzed C-H/N-H activation for the synthesis of N-heterocycles.

Organic letters

Peng X, Wang W, Jiang C, Sun D, Xu Z, Tung CH.
PMID: 25275617
Org Lett. 2014 Oct 17;16(20):5354-7. doi: 10.1021/ol5025426. Epub 2014 Oct 02.

Strained alkynes include arynes and cyclooctynes reacted with N-methoxyamides through palladium-catalyzed C-H/N-H activation for the first time. A variety of important N-heterocycles such as phenanthridinones and isoquinolones were constructed in one step with high efficiency.

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Peng X, Wang W, Jiang C, et al. Strain-promoted oxidative annulation of arynes and cyclooctynes with benzamides: palladium-catalyzed C-H/N-H activation for the synthesis of N-heterocycles. Org Lett. 2014;16(20):5354-7doi: 10.1021/ol5025426.
Peng, X., Wang, W., Jiang, C., Sun, D., Xu, Z., & Tung, C. H. (2014). Strain-promoted oxidative annulation of arynes and cyclooctynes with benzamides: palladium-catalyzed C-H/N-H activation for the synthesis of N-heterocycles. Organic letters, 16(20), 5354-7. https://doi.org/10.1021/ol5025426
Peng, Xianglong, et al. "Strain-promoted oxidative annulation of arynes and cyclooctynes with benzamides: palladium-catalyzed C-H/N-H activation for the synthesis of N-heterocycles." Organic letters vol. 16,20 (2014): 5354-7. doi: https://doi.org/10.1021/ol5025426
Peng X, Wang W, Jiang C, Sun D, Xu Z, Tung CH. Strain-promoted oxidative annulation of arynes and cyclooctynes with benzamides: palladium-catalyzed C-H/N-H activation for the synthesis of N-heterocycles. Org Lett. 2014 Oct 17;16(20):5354-7. doi: 10.1021/ol5025426. Epub 2014 Oct 02. PMID: 25275617.
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A phosphinine 2-carboxaldehyde.

Organic letters

Mao Y, Mathey F.
PMID: 22299589
Org Lett. 2012 Feb 17;14(4):1162-3. doi: 10.1021/ol300113z. Epub 2012 Feb 02.

The first phosphinine 2-carboxaldehyde was synthesized as shown and transformed into an alkene via a Wittig reaction without destruction of the phosphinine ring.

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Mao Y, Mathey F. A phosphinine 2-carboxaldehyde. Org Lett. 2012;14(4):1162-3doi: 10.1021/ol300113z.
Mao, Y., & Mathey, F. (2012). A phosphinine 2-carboxaldehyde. Organic letters, 14(4), 1162-3. https://doi.org/10.1021/ol300113z
Mao, Yanli, and Mathey, Francois. "A phosphinine 2-carboxaldehyde." Organic letters vol. 14,4 (2012): 1162-3. doi: https://doi.org/10.1021/ol300113z
Mao Y, Mathey F. A phosphinine 2-carboxaldehyde. Org Lett. 2012 Feb 17;14(4):1162-3. doi: 10.1021/ol300113z. Epub 2012 Feb 02. PMID: 22299589.
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Decarboxylative allylation of trifluoroethyl sulfones and approach to difluoromethyl compounds.

Organic letters

Shibata N, Fukushi K, Furukawa T, Suzuki S, Tokunaga E, Cahard D.
PMID: 23050610
Org Lett. 2012 Oct 19;14(20):5366-9. doi: 10.1021/ol302589w. Epub 2012 Oct 10.

Allyl carbonates undergo palladium-catalyzed decarboxylative allylation of trifluoroethyl phenyl sulfones. The success of the allylation, which is not efficient under typical strong base-mediated conditions, is the result of mild conditions thanks to a progressive delivery of ethoxide. Indeed, ethyl...

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Shibata N, Fukushi K, Furukawa T, et al. Decarboxylative allylation of trifluoroethyl sulfones and approach to difluoromethyl compounds. Org Lett. 2012;14(20):5366-9doi: 10.1021/ol302589w.
Shibata, N., Fukushi, K., Furukawa, T., Suzuki, S., Tokunaga, E., & Cahard, D. (2012). Decarboxylative allylation of trifluoroethyl sulfones and approach to difluoromethyl compounds. Organic letters, 14(20), 5366-9. https://doi.org/10.1021/ol302589w
Shibata, Norio, et al. "Decarboxylative allylation of trifluoroethyl sulfones and approach to difluoromethyl compounds." Organic letters vol. 14,20 (2012): 5366-9. doi: https://doi.org/10.1021/ol302589w
Shibata N, Fukushi K, Furukawa T, Suzuki S, Tokunaga E, Cahard D. Decarboxylative allylation of trifluoroethyl sulfones and approach to difluoromethyl compounds. Org Lett. 2012 Oct 19;14(20):5366-9. doi: 10.1021/ol302589w. Epub 2012 Oct 10. PMID: 23050610.
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Chlorosulfonamide salts are superior electrophilic chlorine precursors for the organocatalytic asymmetric chlorocyclization of unsaturated amides.

Organic letters

Jaganathan A, Borhan B.
PMID: 24979487
Org Lett. 2014 Jul 18;16(14):3616-9. doi: 10.1021/ol500861z. Epub 2014 Jun 30.

Chloramine-T·3H(2)O and other chlorosulfonamide salts can serve as readily available, stable, and inexpensive precursors of electrophilic chlorine in the organocatalytic asymmetric chlorofunctionalization of olefins. In conjunction with commercially available organocatalysts, they can be utilized in the asymmetric chlorocyclization of...

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Jaganathan A, Borhan B. Chlorosulfonamide salts are superior electrophilic chlorine precursors for the organocatalytic asymmetric chlorocyclization of unsaturated amides. Org Lett. 2014;16(14):3616-9doi: 10.1021/ol500861z.
Jaganathan, A., & Borhan, B. (2014). Chlorosulfonamide salts are superior electrophilic chlorine precursors for the organocatalytic asymmetric chlorocyclization of unsaturated amides. Organic letters, 16(14), 3616-9. https://doi.org/10.1021/ol500861z
Jaganathan, Arvind, and Borhan, Babak. "Chlorosulfonamide salts are superior electrophilic chlorine precursors for the organocatalytic asymmetric chlorocyclization of unsaturated amides." Organic letters vol. 16,14 (2014): 3616-9. doi: https://doi.org/10.1021/ol500861z
Jaganathan A, Borhan B. Chlorosulfonamide salts are superior electrophilic chlorine precursors for the organocatalytic asymmetric chlorocyclization of unsaturated amides. Org Lett. 2014 Jul 18;16(14):3616-9. doi: 10.1021/ol500861z. Epub 2014 Jun 30. PMID: 24979487.
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Nucleopalladation triggering the oxidative Heck reaction: a general strategy to diverse β-indole ketones.

Organic letters

Wang Q, Huang L, Wu X, Jiang H.
PMID: 24237319
Org Lett. 2013 Dec 06;15(23):5940-3. doi: 10.1021/ol4027683. Epub 2013 Nov 15.

A simple and efficient palladium-catalyzed oxidative coupling between 2-alkynyl anilines and allylic alcohols is described by using cheap and green dioxygen as the oxidant. These cross-couplings have a large functional group tolerance and are of higher reactivity toward electron...

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Wang Q, Huang L, Wu X, et al. Nucleopalladation triggering the oxidative Heck reaction: a general strategy to diverse β-indole ketones. Org Lett. 2013;15(23):5940-3doi: 10.1021/ol4027683.
Wang, Q., Huang, L., Wu, X., & Jiang, H. (2013). Nucleopalladation triggering the oxidative Heck reaction: a general strategy to diverse β-indole ketones. Organic letters, 15(23), 5940-3. https://doi.org/10.1021/ol4027683
Wang, Qian, et al. "Nucleopalladation triggering the oxidative Heck reaction: a general strategy to diverse β-indole ketones." Organic letters vol. 15,23 (2013): 5940-3. doi: https://doi.org/10.1021/ol4027683
Wang Q, Huang L, Wu X, Jiang H. Nucleopalladation triggering the oxidative Heck reaction: a general strategy to diverse β-indole ketones. Org Lett. 2013 Dec 06;15(23):5940-3. doi: 10.1021/ol4027683. Epub 2013 Nov 15. PMID: 24237319.
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Ideal bipolar host materials with bis-benzimidazole unit for highly efficient solution-processed green electrophosphorescent devices.

Organic letters

Jiang W, Tang J, Ban X, Sun Y, Duan L, Qiu Y.
PMID: 25260110
Org Lett. 2014 Oct 17;16(20):5346-9. doi: 10.1021/ol502531y. Epub 2014 Sep 26.

An ideal host material with high triplet energy, suitable HOMO energy level, excellent thermal and electrochemical stability, and bipolar charge carrier transport ability was synthesized. A high external quantum efficiency of 13.7% and a luminance efficiency of 48.2 cd...

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Jiang W, Tang J, Ban X, et al. Ideal bipolar host materials with bis-benzimidazole unit for highly efficient solution-processed green electrophosphorescent devices. Org Lett. 2014;16(20):5346-9doi: 10.1021/ol502531y.
Jiang, W., Tang, J., Ban, X., Sun, Y., Duan, L., & Qiu, Y. (2014). Ideal bipolar host materials with bis-benzimidazole unit for highly efficient solution-processed green electrophosphorescent devices. Organic letters, 16(20), 5346-9. https://doi.org/10.1021/ol502531y
Jiang, Wei, et al. "Ideal bipolar host materials with bis-benzimidazole unit for highly efficient solution-processed green electrophosphorescent devices." Organic letters vol. 16,20 (2014): 5346-9. doi: https://doi.org/10.1021/ol502531y
Jiang W, Tang J, Ban X, Sun Y, Duan L, Qiu Y. Ideal bipolar host materials with bis-benzimidazole unit for highly efficient solution-processed green electrophosphorescent devices. Org Lett. 2014 Oct 17;16(20):5346-9. doi: 10.1021/ol502531y. Epub 2014 Sep 26. PMID: 25260110.
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Efficient hydroxymethylation reactions of iodoarenes using CO and 1,3-dimethylimidazol-2-ylidene borane.

Organic letters

Kawamoto T, Okada T, Curran DP, Ryu I.
PMID: 23590524
Org Lett. 2013 May 03;15(9):2144-7. doi: 10.1021/ol4006294. Epub 2013 Apr 16.

A hydroxymethylation reaction of a variety of iodoarenes proceeded effectively in the presence of CO, NHC-borane, diMeImd-BH3 (2) as a radical mediator, and a catalytic amount of AIBN. The reaction took place chemoselectively at the aryl-iodine bond but not...

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Kawamoto T, Okada T, Curran DP, et al. Efficient hydroxymethylation reactions of iodoarenes using CO and 1,3-dimethylimidazol-2-ylidene borane. Org Lett. 2013;15(9):2144-7doi: 10.1021/ol4006294.
Kawamoto, T., Okada, T., Curran, D. P., & Ryu, I. (2013). Efficient hydroxymethylation reactions of iodoarenes using CO and 1,3-dimethylimidazol-2-ylidene borane. Organic letters, 15(9), 2144-7. https://doi.org/10.1021/ol4006294
Kawamoto, Takuji, et al. "Efficient hydroxymethylation reactions of iodoarenes using CO and 1,3-dimethylimidazol-2-ylidene borane." Organic letters vol. 15,9 (2013): 2144-7. doi: https://doi.org/10.1021/ol4006294
Kawamoto T, Okada T, Curran DP, Ryu I. Efficient hydroxymethylation reactions of iodoarenes using CO and 1,3-dimethylimidazol-2-ylidene borane. Org Lett. 2013 May 03;15(9):2144-7. doi: 10.1021/ol4006294. Epub 2013 Apr 16. PMID: 23590524.
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Cu(I)-NHC catalyzed asymmetric silyl transfer to unsaturated lactams and amides.

Organic letters

Pace V, Rae JP, Procter DJ.
PMID: 24350760
Org Lett. 2014 Jan 17;16(2):476-9. doi: 10.1021/ol4033623. Epub 2013 Dec 18.

The first asymmetric silylation of unsaturated lactams and amides using Cu(I)-NHC catalysts and PhMe2SiBpin has been accomplished. The method has been exploited in an expedient asymmetric synthesis of the (R)-enantiomer of the nootropic drug oxiracetam.

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Pace V, Rae JP, Procter DJ. Cu(I)-NHC catalyzed asymmetric silyl transfer to unsaturated lactams and amides. Org Lett. 2013;16(2):476-9doi: 10.1021/ol4033623.
Pace, V., Rae, J. P., & Procter, D. J. (2014). Cu(I)-NHC catalyzed asymmetric silyl transfer to unsaturated lactams and amides. Organic letters, 16(2), 476-9. https://doi.org/10.1021/ol4033623
Pace, Vittorio, et al. "Cu(I)-NHC catalyzed asymmetric silyl transfer to unsaturated lactams and amides." Organic letters vol. 16,2 (2014): 476-9. doi: https://doi.org/10.1021/ol4033623
Pace V, Rae JP, Procter DJ. Cu(I)-NHC catalyzed asymmetric silyl transfer to unsaturated lactams and amides. Org Lett. 2014 Jan 17;16(2):476-9. doi: 10.1021/ol4033623. Epub 2013 Dec 18. PMID: 24350760.
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Free-radical cascade alkylarylation of alkenes with simple alkanes: highly efficient access to oxindoles via selective (sp3)C-H and (sp2)C-H bond functionalization.

Organic letters

Li Z, Zhang Y, Zhang L, Liu ZQ.
PMID: 24354601
Org Lett. 2014 Jan 17;16(2):382-5. doi: 10.1021/ol4032478. Epub 2013 Dec 19.

A copper-catalyzed alkylarylation of alkenes with simple alkanes was achieved, which not only provided an efficient method to prepare various alkyl-substituted oxindoles, but also represented a novel strategy for selective sp(3) C-H functionalization/C-C bond formation via a free-radical cascade...

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Li Z, Zhang Y, Zhang L, et al. Free-radical cascade alkylarylation of alkenes with simple alkanes: highly efficient access to oxindoles via selective (sp3)C-H and (sp2)C-H bond functionalization. Org Lett. 2013;16(2):382-5doi: 10.1021/ol4032478.
Li, Z., Zhang, Y., Zhang, L., & Liu, Z. Q. (2014). Free-radical cascade alkylarylation of alkenes with simple alkanes: highly efficient access to oxindoles via selective (sp3)C-H and (sp2)C-H bond functionalization. Organic letters, 16(2), 382-5. https://doi.org/10.1021/ol4032478
Li, Zejiang, et al. "Free-radical cascade alkylarylation of alkenes with simple alkanes: highly efficient access to oxindoles via selective (sp3)C-H and (sp2)C-H bond functionalization." Organic letters vol. 16,2 (2014): 382-5. doi: https://doi.org/10.1021/ol4032478
Li Z, Zhang Y, Zhang L, Liu ZQ. Free-radical cascade alkylarylation of alkenes with simple alkanes: highly efficient access to oxindoles via selective (sp3)C-H and (sp2)C-H bond functionalization. Org Lett. 2014 Jan 17;16(2):382-5. doi: 10.1021/ol4032478. Epub 2013 Dec 19. PMID: 24354601.
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Indium-Catalyzed [2 + 2] Cycloaddition of Allylsilanes to Internal Alkynones.

Organic letters

Okamoto K, Shimbayashi T, Tamura E, Ohe K.
PMID: 26584237
Org Lett. 2015 Dec 04;17(23):5843-5. doi: 10.1021/acs.orglett.5b03065. Epub 2015 Nov 19.

We have developed an indium-catalyzed [2 + 2] cycloaddition of allylsilanes to alkynones leading to selective cyclobutenone formation. The resulting cyclobutenones were readily converted to the oxidized products by Tamao-Fleming oxidation or the ring-opened products by an electrocyclic reaction.

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Okamoto K, Shimbayashi T, Tamura E, et al. Indium-Catalyzed [2 + 2] Cycloaddition of Allylsilanes to Internal Alkynones. Org Lett. 2015;17(23):5843-5doi: 10.1021/acs.orglett.5b03065.
Okamoto, K., Shimbayashi, T., Tamura, E., & Ohe, K. (2015). Indium-Catalyzed [2 + 2] Cycloaddition of Allylsilanes to Internal Alkynones. Organic letters, 17(23), 5843-5. https://doi.org/10.1021/acs.orglett.5b03065
Okamoto, Kazuhiro, et al. "Indium-Catalyzed [2 + 2] Cycloaddition of Allylsilanes to Internal Alkynones." Organic letters vol. 17,23 (2015): 5843-5. doi: https://doi.org/10.1021/acs.orglett.5b03065
Okamoto K, Shimbayashi T, Tamura E, Ohe K. Indium-Catalyzed [2 + 2] Cycloaddition of Allylsilanes to Internal Alkynones. Org Lett. 2015 Dec 04;17(23):5843-5. doi: 10.1021/acs.orglett.5b03065. Epub 2015 Nov 19. PMID: 26584237.
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Highly Enantioselective Construction of Fluoroalkylated Quaternary Stereocenters via Organocatalytic Dehydrated Mannich Reaction of Unprotected Hemiaminals with Ketones.

Organic letters

Zhang S, Li L, Hu Y, Li Y, Yang Y, Zha Z, Wang Z.
PMID: 26414655
Org Lett. 2015 Oct 16;17(20):5036-9. doi: 10.1021/acs.orglett.5b02514. Epub 2015 Sep 28.

A general organocatalytic asymmetric dehydrated Mannich reaction of fluoroalkyl hemiaminals with ketones is reported. In this Mannich reaction, previously less explored aryl ketones showed great reactivity. By virtue of this efficient method, a wide range of biologically active β-amino...

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Zhang S, Li L, Hu Y, et al. Highly Enantioselective Construction of Fluoroalkylated Quaternary Stereocenters via Organocatalytic Dehydrated Mannich Reaction of Unprotected Hemiaminals with Ketones. Org Lett. 2015;17(20):5036-9doi: 10.1021/acs.orglett.5b02514.
Zhang, S., Li, L., Hu, Y., Li, Y., Yang, Y., Zha, Z., & Wang, Z. (2015). Highly Enantioselective Construction of Fluoroalkylated Quaternary Stereocenters via Organocatalytic Dehydrated Mannich Reaction of Unprotected Hemiaminals with Ketones. Organic letters, 17(20), 5036-9. https://doi.org/10.1021/acs.orglett.5b02514
Zhang, Sheng, et al. "Highly Enantioselective Construction of Fluoroalkylated Quaternary Stereocenters via Organocatalytic Dehydrated Mannich Reaction of Unprotected Hemiaminals with Ketones." Organic letters vol. 17,20 (2015): 5036-9. doi: https://doi.org/10.1021/acs.orglett.5b02514
Zhang S, Li L, Hu Y, Li Y, Yang Y, Zha Z, Wang Z. Highly Enantioselective Construction of Fluoroalkylated Quaternary Stereocenters via Organocatalytic Dehydrated Mannich Reaction of Unprotected Hemiaminals with Ketones. Org Lett. 2015 Oct 16;17(20):5036-9. doi: 10.1021/acs.orglett.5b02514. Epub 2015 Sep 28. PMID: 26414655.
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2,2,2-Trifluoroethylation of Styrenes with Concomitant Introduction of a Hydroxyl Group from Molecular Oxygen by Photoredox Catalysis Activated by Visible Light.

Organic letters

Li L, Huang M, Liu C, Xiao JC, Chen QY, Guo Y, Zhao ZG.
PMID: 26361093
Org Lett. 2015 Oct 02;17(19):4714-7. doi: 10.1021/acs.orglett.5b02177. Epub 2015 Sep 11.

The visible-light-induced photoredox difunctionalization reactions of styrenes with 1,1,1-trifluoro-2-iodoethane under an oxygen atmosphere in the presence of water give γ-trifluoromethyl alcohols. In this radical reaction, the oxygen atom in the product originates from molecular oxygen, and water is shown...

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Li L, Huang M, Liu C, et al. 2,2,2-Trifluoroethylation of Styrenes with Concomitant Introduction of a Hydroxyl Group from Molecular Oxygen by Photoredox Catalysis Activated by Visible Light. Org Lett. 2015;17(19):4714-7doi: 10.1021/acs.orglett.5b02177.
Li, L., Huang, M., Liu, C., Xiao, J. C., Chen, Q. Y., Guo, Y., & Zhao, Z. G. (2015). 2,2,2-Trifluoroethylation of Styrenes with Concomitant Introduction of a Hydroxyl Group from Molecular Oxygen by Photoredox Catalysis Activated by Visible Light. Organic letters, 17(19), 4714-7. https://doi.org/10.1021/acs.orglett.5b02177
Li, Lun, et al. "2,2,2-Trifluoroethylation of Styrenes with Concomitant Introduction of a Hydroxyl Group from Molecular Oxygen by Photoredox Catalysis Activated by Visible Light." Organic letters vol. 17,19 (2015): 4714-7. doi: https://doi.org/10.1021/acs.orglett.5b02177
Li L, Huang M, Liu C, Xiao JC, Chen QY, Guo Y, Zhao ZG. 2,2,2-Trifluoroethylation of Styrenes with Concomitant Introduction of a Hydroxyl Group from Molecular Oxygen by Photoredox Catalysis Activated by Visible Light. Org Lett. 2015 Oct 02;17(19):4714-7. doi: 10.1021/acs.orglett.5b02177. Epub 2015 Sep 11. PMID: 26361093.
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Showing 1 to 12 of 18218 entries