有機反応設計研究室

Laboratory of Organic Reaction Design and Synthesis

Recent Publications of Our Group

     

2020~

58. Regioselective Silylations of Propargyl and Allyl Pivalates through Ca-Promoted Reductive C(sp3)-O Bond Cleavage.
Zhang, T. Zheng, S. Kobayashi, T. Maekawa, H., Org. Lett. 2021, 23, in press. doi.org/10.1021/acs.orglett.1c02532


57. Reductive 3-Silylation of Benzofuran Derivatives via Coupling Reaction with Chlorotrialkylsilane.
Zheng, S., Zhang, T., Maekawa, H., J. Org. Chem. 2020, 85, 13965-13972


56. A Simple Protocol from Benzalacetones to 1,1,1‐Trifluoro‐2,5‐diketones and 2‐(Trifluoromethyl) furans by Reductive Trifluoroacetylation.
Zhang, T., Xie, C., Sakata, H., Nakajima, K., Shimoyama, T., Watanabe, T., Maekawa, H., Eur. J. Org. Chem. 2020, 2237-2243.
     

2010~2019

55. Construction of a CF3-Containing Benzofurofuranone Skeleton from Coumarins via Reductive Coupling and Acid-Mediated Ring Contraction.
Zhang, T., Shimizu, Y., Fukaya, S., Sawa, T., Maekawa, H., J. Org. Chem. 2019, 84, 12165-12171.


54. Selective Introduction of Trifluoroacetyl Group to β- and δ-Position of Aromatic Conjugated Esters: Facile Synthesis of Fluorine-containing Keto Esters. (Selected as front cover)
Zhang, T., Shimizu, Y., Shimizu, K., Abe, M., Zheng, S., Maekawa, H., Asian J. Org. Chem. 2019, 8, 344-347.


53. Catalyst-Free and Solvent-Controlled Reductive Coupling of Activated Vinyl Triflates with Chlorotrimethylsilane by Magnesium Metal and Its Synthetic Application.
Maekawa, H., Noda, K., Kuramochi, K., Zhang, T., Org. Lett. 2018, 20, 1953-1956.


52. Synthesis of 4-(Trifluoromethyl)cyclopentenones and 2-(Trifluoromethyl)furans by Reductive Trifluoroacetylation of Ynones.
Zhang, T., Maekawa, H., Org. Lett. 2017, 19, 6602-6605.


51. (Review) Novel development of carbon-carbon bond and carbon-silicon bond formation by magnesium-promoted reduction.
Maekawa, H., J. Syn. Org. Chem. Jpn. 2017, 75, 240-252.

50. Reductive carboxylation of aromatic esters by electron transfer from magnesium metal.
Maekawa, H., Okawara, H., Murakami, T., Tetrahedron Lett. 2017, 58, 206-209.
49. Facile and highly selective silylation of vinylpyridines at the β-olefinic carbon by magnesium-promoted reduction.
Zhang, T., Zhang, Z., Nishiyama, Y., Maekawa, H., Tetrahedron 2016, 72, 2293-2299.


48. Selective introduction of a trifluoroacetyl group onto 4-vinylpyridines through magnesium-promoted reduction.
Maekawa, H., Nishiyama, Y., Tetrahedron 2015, 71, 6694-6700.


47. Magnesium-promoted reductive acylation of aromatic conjugated ynones accompanying with transposition of the triple bond.
Zhang, T., Takano, A., Nishiyama, Y., Maekawa, H., Tetrahedron 2015, 71, 2629-2635.


46. Facile synthesis of multifunctionalized allenes by magnesium-promoted reductive silylation of aromatic conjugated ynones.
Maekawa, H., Takano, A., Watanabe, M., Tetrahedron Lett. 2014, 55, 6208-6211.


45. Facile synthesis of aromatic unsymmetrical fluorine-containing acyloins through the reductive trifluoroacetylation of benzaldehyde and transposition of the carbonyl group.
Maekawa, H., Kudo, M., Nishiyama, Y., Shimizu, K., Abe, M., Tetrahedron 2014, 70, 2081-2087.


44. Magnesium-promoted reductive silylation and acylation of tropone and tropone acetal.
Maekawa, H., Nagakubo, K., Nishi, M., Nishimura, M., Nagahara, D., Bull. Chem. Soc. Jpn. 2013, 86, 1183-1189.

43. Anodic cyanation of arylsilanes without elimination of silyl groups.
Maekawa, H., Nakamura, T., Yamaguchi, A., Electrochemistry 2013, 81, 394-398.

42. Regioselective coupling reaction of azulene with α,β-unsaturated ketones by Mg-promoted reduction.
Maekawa, H., Honda, J., Akaba, R., Tetrahedron Lett. 2012, 53, 6519-6522.

41. Abnormal and direct para-trifluoroacetylation of branched alkyl phenyl ketones by Mg-promoted reductive aromatic substitution.
Maekawa, H., Ozaki, T., Zulkeflee, D., Murakami, T., Kihara, S., Nishiguchi, I., Synlett 2012, 23, 401-404.

40. Practical synthesis of diethyl phenylsuccinate by Mg-promoted carboxylation of ethyl cinnamate.
Maekawa, H., Murakami, T., Miyazaki, T., Nishiguchi, I., Chem. Lett. 2011, 40, 368-369.

39. Novel synthesis of 1,4-dialkoxy-5,6,7,8-multi-substituted-2,3-dicyanonaphthalenes through electron transfer from Mg-metal and efficient development of new naphthalocyanines.
Miyazaki, T., Harada, A., Maekawa, H., Yamamoto, Y., Nishiguchi, I., Synlett 2011, 22, 862-868.

38. Mg-promoted facile and selective intramolecular cyclization of aromatic δ-ketoesters.
Miyazaki, T., Maekawa, H., Yonemura, K., Yamamoto, Y., Yamanaka, Y., Nishiguchi, I., Tetrahedron 2011, 67, 1598-1602.

37. Highly stereo-and regio-selective intramolecular cyclization with diastereoselective asymmetric induction by electroreduction of optically active N-alkenyl-2-acylpyrrolidines.
Miyazaki, T., Maekawa, H., Hisatomi, T., Nishiguchi, I., Electrochemistry 2011, 79, 447-449.

36. (Review) New progress in organic synthesis through organic electron transfer chemistry.
Nishiguchi, I., J. Syn. Org. Chem. jpn. 2010, 68, 824-833.

35. Mg-promoted C-trifluoroacetylation of benzophenone.
Maekawa, H., Ozaki, T., Nishiguchi, I., Tetrahedron Lett. 2010, 51, 796-799.
    

Selected publications 1997~2009

34. Zn-promoted regio- and sequence-selective one-pot joining reactions of three components: vinylpyridines, alkyl iodides, and carbonyl compounds (or nitriles).
Mineyama, K., Maekawa, H., Kohsaka, A., Yamamoto, Y., Nishiguchi, I., Tetrahedron 2009, 65, 7706-7711.

33. Some progress and development on synthetic electroorganic chemistry.
Nishiguchi, ECS Transactions 2007, 2, 19-24.

32. Synthesis of methyl aziridine 2-carboxylate through electroreductive cross coupling of methyl gem-trichloroacetate with aromatic imines.
Nishiguchi, I., Kendrekar, P.S., Maekawa, H., ECS Transactions 2007, 6, 1-7.

31. Carbon-acylation of benzoic anhydride derivatives by electroreduction.
Nishiguchi, I., Matsunami, M., Mizoguchi, S., Maekawa, H., ECS Transactions 2007, 2, 29-32.

30. Magnesium-promoted one-pot double C-acylation and cycloaddition of anthracene and double C-acylation of benzyl acrylates.
Matsunami, M., Sakai, N., Morimoto, T., Maekawa, H., Nishiguchi, I., Synlett 2007, 769-774.

29. Stereoselective synthesis of spiro-lactones possessing cyclopropane rings through electroreductive cross coupling of styrene derivatives with diphenyl succinate or glutarate.
Kendrekar, P.S., Yamamoto, Y., Dhiman, A., Maekawa, H., Nishiguchi, I.,Electrochemistry 2007, 75, 813-818.

28. Mg-promoted reductive coupling of aromatic carbonyl compounds with trimethylsilyl chloride and bis(chloromethylsilyl) compounds.
Uchida, T., Kita, Y., Maekawa, H., Nishiguchi, I., Tetrahedron 2006, 62, 3103-3111.

27. Preparation and characterization of (5-methyl-2-oxo-1,3-dioxol-4-yl) methyl thiamine sulfides.
Uchida, T., Tsukamoto, G., Yamamoto, K., Kametani, S.-I, Maekawa, H., Nishiguchi, I., YAKUGAKU ZASSHI 2006, 126, 179-186.

26. One-pot vicinal and geminal double carboalkoxylation with N-carboalkoxy-imidazole by electroreduction of aromatic vinyl and imine derivatives.
Nishiguchi, I., Sunderrao, K.P., Yamamoto, U., Yamamoto, Y., Uchida, T., Maekawa, H., Electrochemistry 2006, 74, 680-684.

25. Synthesis and behavior of novel phthalocyanines possessing intramolecular crown ether bridges between their different aromatic rings for effective extraction multi metal inclusion.
Matsunami, M., Takaki, A., Maekawa, H., Nishiguchi, I., Sci. Technol. Adv. Mat. 2005, 6, 172-180.

24. Electroreductive one-pot double carboalkoxylation with N- carboalkoxyimidazole.
Nishiguchi, I., Uchida, T., Yamamoto, U., Maekawa, H., Proceedings - Electrochemical Society. 2004, 10, 117-120.

23. Unprecedented and unique electroreductive rearrangement of 4-(2-nitrophenyl)-3,5-dicarboalkoxy-1,4-dihydro-pyridines to 3-carboalkoxyquinolines.
Nishiguchi, I., Maseguchi, M., Matsunami, M., Yamamoto, Y., Maekawa, H., Proceedings - Electrochemical Society. 2004, 10, 137-140.

22. Mg-promoted mixed pinacol coupling.
Maekawa, H., Yamamoto, Y., Shimada, H., Yonemura, K., Nishiguchi, I., Tetrahedron Lett. 2004, 45, 3869-3872.

21. Zn-promoted regioselective and sequence-selective one-pot joining reaction of three components: alkyl iodides, α,β-unsaturated esters (or nitriles), and acylating agents.
Yamamoto, Y., Nakano, S., Maekawa, H., Nishiguchi, I., Org. Lett. 2004, 6, 799-802.

20. Regioselective synthesis of bis(silyl enol ethers) and bis(conjugated enones) through electron transfer from Mg metal.
Maekawa, H., Sakai, M., Uchida, T., Kita, Y., Nishiguchi, I., Tetrahedron Lett. 2004, 45, 607-609.

19. Mg-promoted regioselective cross-coupling of stilbene derivatives with carbonyl compounds.
Yamamoto, Y., Kawano, S., Maekawa, H., Nishiguchi, I., Synlett 2004, 30-36.

18. Novel one-pot vicinal double C-acylation of styrenes and methacrylates by electroreduction.
Yamamoto, Y., Maekawa, H., Goda, S., Nishiguchi, I., Org. Lett. 2003, 5, 2755-2758.

17. Intramolecular electroreductive cyclization of heteroatom-containing non-conjugated enones and ynones.
Goda, S., Yamada, K., Yamamoto, Y., Maekawa, H., Nishiguchi, I., J. Electroanal. Chem. 2003, 545, 129-140.

16. Enantioselective electrochemical oxidation of enol acetates using a chiral supporting electrolyte.
Maekawa, H., Itoh, K., Goda, S., Nishiguchi, I., Chirality 2003, 15, 95-100.

15. Stereoselectivity in intramolecular cyclization of non-conjugated unsaturated ketones by electroreduction.
Nishiguchi, I., Goda, S., Yamada, K., Yamamoto, Y., Maekawa, H., Chem. Lett. 2002, 1254-1255.

14. Mg-promoted stereoselective desulfonation of β-arylvinyl sulfone derivatives.
Nishiguchi, I., Matsumoto, T., Kuwahara, T., Kyoda, M., Maekawa, H., Chem. Lett. 2002, 478-479.

13. Mg-promoted regioselective carbon-silylation of α-phosphonoacrylate derivatives.
Kyoda, M., Yokoyama, T., Kuwahara, T., Maekawa, H., Nishiguchi, I., Chem. Lett. 2002, 228-229.

12. Mg-promoted carbon-acylation of aromatic aldehydes and ketones.
Nishiguchi, I., Sakai, M., Maekawa, H., Ohno, T., Yamamoto, Y., Ishino, Y., Tetrahedron Lett. 2002, 43, 635-637.

11. Regioselective Mg-promoted C-acylation of stilbene and acenaphthylene derivatives.
Nishiguchi,I., Yamamoto, Y., Sakai, M., Ohno, T., Ishino, Y., Maekawa, H., Synlett 2002, 759-762.

10. Mg-promoted regio- and stereoselective C-acylation of aromatic α,β-unsaturated carbonyl compounds.
Ohno, T., Sakai, M., Ishino, Y., Shibata, T., Maekawa, H., Nishiguchi, I., Org. Lett. 2001, 3, 3439-3442.

9. Novel synthesis of 2-arylcyclohexanones using anodic oxidation of enol esters as the key step.
Itoh, K., Shino, S., Maekawa, H., Nishiguchi, I., J. Electroanal. Chem. 2001, 507, 14-21.

8. Selective synthesis of α-chloroepoxides by electroreductive cross-coupling of methyl trichloroacetate with aliphatic aldehydes using reactive metal anodes.
Nishiguchi, I., Goda, S., Kikkawa, T., Ishino, Y., Maekawa, H., J. Electroanal. Chem. 2001, 507, 185-190.

7. Highly selective and facile synthesis of dihydro- and tetrahydropyridine dicarboxylic acid derivatives using electroreduction as a key step.
Kita, Y., Maekawa, H., Yamasaki, Y., Nishiguchi, I., Tetrahedron 2001, 57, 2095-2102.

6. Regioselective C-acylation of vinylphosphorus compounds through electroreduction or Mg-promoted reduction.
Kyoda, M., Yokoyama, T., Maekawa, H., Ohno, T., Nishiguchi, I., Synlett 2001, 1535-1538.

5. Electrochemical hydrocoupling of acetylene derivatives by anodic oxidation of NaBH4.
Nishiguchi, I., Itoh, K., Maekawa, H., Electrochim. Acta 2000, 45, 2991-2993.

4. Facile iodination of terminal acetylenes by anodic oxidation in the presence of NaI.
Nishiguchi, I., Kanbe, O., Itoh, K., Maekawa, H., Synlett 2000, 89-91.

3. Facile O-silylation of tertiary alcohols in the presence of Mg-metal.
Nishiguchi, I., Kita, Y., Watanabe, M., Ishino, Y., Ohno, T., Maekawa, H., Synlett 2000, 1025-1027.

2. Selective and facile electroreductive synthesis of dihydro- and tetrahydropyridine dicarboxylic acid derivatives.
Kita, Y., Maekawa, H., Yamasaki, Y., Nishiguchi, I., Tetrahedron Lett. 1999, 40, 8587-8590.

1. Facile synthesis of silyl enol ethers by Mg-promoted coupling of aliphatic carbonyl compounds with trimethylchlorosilane.
Ishino, Y., Kita, Y., Maekawa, H., Ohno, T., Yamasaki, Y., Miyata, T., Nishiguchi, I., Tetrahedron Lett. 1999, 40, 1349-1352.

Books and Reviews on Organic Electron Transfer Reactions

5. H. Maekawa, Encyclopedia of Applied Electrochemistry, K. Ohta, G. Kreysa, R. F. Savinell, eds., Chapter371, Reactive Metal Electrode, Springer Science, New York, pp1772-1775 (2014)
4. 前川博史、マグネシウム金属還元による芳香族ケトンへのトリフルオロアセチル基導入法、化学工業、2012,63(4)、59-65.
3. 前川博史、山本祥正、西口郁三、反応性金属陽極を用いた電極還元アシル化反応、電気化学および工業物理化学,2010,78(3),208-212.
2. 西口郁三、前川博史、有機電解合成の新展開、淵上寿雄監修、3章、3担当、pp45-53.(シーエムシー出版)(2004)
1. 前川博史、西口郁三、反応性金属陽極を用いた新規炭素-炭素結合形成を目指す有機電解反応、電気化学および工業物理化学,1999,67(8),875-877.