메뉴 건너뛰기




Volumn 8, Issue 12, 2016, Pages 1131-1136

Benzazetidine synthesis via palladium-catalysed intramolecular C-H amination

Author keywords

[No Author keywords available]

Indexed keywords


EID: 84996503633     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.2585     Document Type: Article
Times cited : (97)

References (30)
  • 1
    • 0036374173 scopus 로고    scopus 로고
    • Aziridines: Epoxides' ugly cousins
    • Sweeney, J. B. Aziridines: epoxides' ugly cousins Chem. Soc. Rev. 31, 247-258 (2002).
    • (2002) Chem. Soc. Rev. , vol.31 , pp. 247-258
    • Sweeney, J.B.1
  • 2
    • 53549128637 scopus 로고    scopus 로고
    • Novel syntheses of azetidines and azetidinones
    • Brandi, A., Cicchi, S., Cordero, F. M. Novel syntheses of azetidines and azetidinones. Chem. Rev. 108, 3988-4035 (2008).
    • (2008) Chem. Rev. , vol.108 , pp. 3988-4035
    • Brandi, A.1    Cicchi, S.2    Cordero, F.M.3
  • 3
    • 78650162473 scopus 로고    scopus 로고
    • Highly reactive 4-membered ring nitrogen-containing heterocycles: Synthesis and properties
    • Alcaide, B., Almendros, P., Aragoncillo, C. Highly reactive 4-membered ring nitrogen-containing heterocycles: synthesis and properties. Curr. Opin. Drug Discov. Devel. 13, 685-697 (2010).
    • (2010) Curr. Opin. Drug Discov. Devel. , vol.13 , pp. 685-697
    • Alcaide, B.1    Almendros, P.2    Aragoncillo, C.3
  • 4
    • 0035793265 scopus 로고    scopus 로고
    • A Rh-catalyzed CH insertion reaction for the oxidative conversion of carbamates to oxazolidinones
    • Espino, C. G., Du Bois, J. A Rh-catalyzed CH insertion reaction for the oxidative conversion of carbamates to oxazolidinones. Angew. Chem. Int. Ed. 40, 598-600 (2001).
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 598-600
    • Espino, C.G.1    Du Bois, J.2
  • 5
    • 84877354471 scopus 로고    scopus 로고
    • Complex N-heterocycle synthesis via ironcatalyzed direct C-H bond amination
    • Hennessy, E. T., Betley, T. A. Complex N-heterocycle synthesis via ironcatalyzed direct C-H bond amination. Science 340, 591-595 (2013).
    • (2013) Science , vol.340 , pp. 591-595
    • Hennessy, E.T.1    Betley, T.A.2
  • 6
    • 84885070397 scopus 로고    scopus 로고
    • Intramolecular C(sp3)-H amination
    • Jeffrey, J. L., Sarpong, R. Intramolecular C(sp3)-H amination. Chem. Sci. 4, 4092-4106 (2013).
    • (2013) Chem. Sci. , vol.4 , pp. 4092-4106
    • Jeffrey, J.L.1    Sarpong, R.2
  • 7
    • 27144450136 scopus 로고    scopus 로고
    • Combined C-H functionalization/C-N bond formation route to carbazoles
    • Tsang, P.W. C., Zheng, N., Buchwald, S. L. Combined C-H functionalization/C-N bond formation route to carbazoles. J. Am. Chem. Soc. 127, 14560-14561 (2005).
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 14560-14561
    • Tsang, P.W.C.1    Zheng, N.2    Buchwald, S.L.3
  • 8
    • 54849436434 scopus 로고    scopus 로고
    • Synthesis of and-lactams via Pd(II)-catalyzed C-H activation reactions
    • Wasa, M., Yu, J.-Q. Synthesis of, and-lactams via Pd(II)-catalyzed C-H activation reactions. J. Am. Chem. Soc. 130, 14058-14059 (2008).
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 14058-14059
    • Wasa, M.1    Yu, J.-Q.2
  • 9
    • 84902000334 scopus 로고    scopus 로고
    • Palladium-catalysed C-H activation of aliphatic amines to give strained nitrogen heterocycles
    • McNally, A., Haffemayer, B., Collins, B. S. L., Gaunt, M. J. Palladium-catalysed C-H activation of aliphatic amines to give strained nitrogen heterocycles. Nature 510, 129-133 (2014).
    • (2014) Nature , vol.510 , pp. 129-133
    • McNally, A.1    Haffemayer, B.2    Collins, B.S.L.3    Gaunt, M.J.4
  • 10
    • 67649488045 scopus 로고    scopus 로고
    • Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: Versatility and practicality
    • Chen, X., Engle, K. M., Wang, D.-H., Yu, J.-Q. Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality. Angew. Chem. Int. Ed. 48, 5094-5115 (2009).
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 5094-5115
    • Chen, X.1    Engle, K.M.2    Wang, D.-H.3    Yu, J.-Q.4
  • 11
    • 77949381429 scopus 로고    scopus 로고
    • Palladium-catalyzed ligand-directed C-H functionalization reactions
    • Lyons, T. W., Sanford, M. S. Palladium-catalyzed ligand-directed C-H functionalization reactions. Chem. Rev. 110, 1147-1169 (2010).
    • (2010) Chem. Rev. , vol.110 , pp. 1147-1169
    • Lyons, T.W.1    Sanford, M.S.2
  • 12
    • 84859616806 scopus 로고    scopus 로고
    • High-valent organometallic copper and palladium in catalysis
    • Hickman, A. J., Sanford, M. S. High-valent organometallic copper and palladium in catalysis. Nature 484, 177-185 (2012).
    • (2012) Nature , vol.484 , pp. 177-185
    • Hickman, A.J.1    Sanford, M.S.2
  • 13
    • 79851471855 scopus 로고    scopus 로고
    • Bystanding F+ oxidants enable selective reductive elimination from high-valent metal centers in catalysis
    • Engle, K. M., Mei, T.-S., Wang, X., Yu, J.-Q. Bystanding F+ oxidants enable selective reductive elimination from high-valent metal centers in catalysis. Angew. Chem. Int. Ed. 50, 1478-1491 (2011).
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 1478-1491
    • Engle, K.M.1    Mei, T.-S.2    Wang, X.3    Yu, J.-Q.4
  • 14
    • 0034787694 scopus 로고    scopus 로고
    • Aza-ortho-xylylenes in organic synthesis
    • Wojciechowski, K. Aza-ortho-xylylenes in organic synthesis. Eur. J. Org. Chem. 3587-3605 (2001).
    • (2001) Eur. J. Org. Chem. , pp. 3587-3605
    • Wojciechowski, K.1
  • 15
  • 17
    • 0024784625 scopus 로고
    • Displacements at the nitrogen of lithio-alkoxylamides by organometallic reagents
    • Beak, P., Selling, G. W. Displacements at the nitrogen of lithio-alkoxylamides by organometallic reagents. J. Org. Chem. 54, 5574-5580 (1989).
    • (1989) J. Org. Chem. , vol.54 , pp. 5574-5580
    • Beak, P.1    Selling, G.W.2
  • 18
    • 37049111032 scopus 로고
    • Preparation and some reactions of benzazetidines
    • Lancaster, M., Smith, D. J. H. Preparation and some reactions of benzazetidines. Chem. Commun. 471-472 (1980).
    • (1980) Chem. Commun. , pp. 471-472
    • Lancaster, M.1    Smith, D.J.H.2
  • 19
    • 84855643302 scopus 로고    scopus 로고
    • Heterocycle synthesis via direct CH/NH coupling
    • Nadres, E. T., Daugulis, O. Heterocycle synthesis via direct CH/NH coupling. J. Am. Chem. Soc. 134, 7-10 (2012).
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 7-10
    • Nadres, E.T.1    Daugulis, O.2
  • 20
    • 84862908390 scopus 로고    scopus 로고
    • Highly efficient syntheses of azetidines, pyrrolidines, and indolines via palladium-catalyzed intramolecular amination of C(sp3)-H and C(sp2)-H bonds at the and positions
    • He, G., Zhao, Y., Zhang, S., Lu, C., Chen, G. Highly efficient syntheses of azetidines, pyrrolidines, and indolines via palladium-catalyzed intramolecular amination of C(sp3)-H and C(sp2)-H bonds at the and positions. J. Am. Chem. Soc. 134, 3-6 (2012).
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 3-6
    • He, G.1    Zhao, Y.2    Zhang, S.3    Lu, C.4    Chen, G.5
  • 21
    • 84885447016 scopus 로고    scopus 로고
    • Use of a readily removable auxiliary group for the synthesis of pyrrolidones by the palladium-catalyzed intramolecular amination of unactivated C(sp3)H bonds
    • He, G., Zhang, S., Nack, W. A., Chen, G. Use of a readily removable auxiliary group for the synthesis of pyrrolidones by the palladium-catalyzed intramolecular amination of unactivated C(sp3)H bonds. Angew. Chem. Int. Ed. 52, 11124-11128 (2013).
    • (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 11124-11128
    • He, G.1    Zhang, S.2    Nack, W.A.3    Chen, G.4
  • 22
    • 84882775049 scopus 로고    scopus 로고
    • Developing ligands for palladium(II)-catalyzed C-H functionalization
    • Engle, K. M., Yu., J.-Q. Developing ligands for palladium(II)-catalyzed C-H functionalization. J. Org. Chem. 78, 8927-8955 (2013).
    • (2013) J. Org. Chem. , vol.78 , pp. 8927-8955
    • Engle, K.M.1    Yu, J.-Q.2
  • 23
    • 72849149530 scopus 로고    scopus 로고
    • Palladium-catalyzed aryl C-H bonds activation/acetoxylation utilizing a bidentate system
    • Gou, F.-R. et al. Palladium-catalyzed aryl C-H bonds activation/acetoxylation utilizing a bidentate system. Org. Lett. 11, 5726-5729 (2009).
    • (2009) Org. Lett. , vol.11 , pp. 5726-5729
    • Gou, F.-R.1
  • 24
    • 81755176481 scopus 로고    scopus 로고
    • Participation of carbonyl oxygen in carbon-carboxylate bond-forming reductive elimination from palladium
    • Gary, J. B., Sanford, M. S. Participation of carbonyl oxygen in carbon-carboxylate bond-forming reductive elimination from palladium. Organometallics 30, 6143-6149 (2011).
    • (2011) Organometallics , vol.30 , pp. 6143-6149
    • Gary, J.B.1    Sanford, M.S.2
  • 25
    • 84873392053 scopus 로고    scopus 로고
    • Chemoselectivity in the reductive elimination from high oxidation state palladium complexes-scrambling mechanism uncovered
    • Nielsen, M. C., Lyngvi, E., Schoenebeck, F. Chemoselectivity in the reductive elimination from high oxidation state palladium complexes-scrambling mechanism uncovered. J. Am. Chem. Soc. 135, 1978-1985 (2013).
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 1978-1985
    • Nielsen, M.C.1    Lyngvi, E.2    Schoenebeck, F.3
  • 26
    • 59049089106 scopus 로고    scopus 로고
    • Chemistry of polyvalent iodine
    • Zhdankin, V. V., Stang, P. J. Chemistry of polyvalent iodine. Chem. Rev. 108, 5299-5358 (2008).
    • (2008) Chem. Rev. , vol.108 , pp. 5299-5358
    • Zhdankin, V.V.1    Stang, P.J.2
  • 27
    • 77949784030 scopus 로고    scopus 로고
    • Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds
    • Shabashov, M., Daugulis, O. Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds. J. Am. Chem. Soc. 132, 3965-3972 (2010).
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 3965-3972
    • Shabashov, M.1    Daugulis, O.2
  • 28
    • 68249136644 scopus 로고    scopus 로고
    • Synthetic and mechanistic studies of Pd-catalyzed CH arylation with diaryliodonium salts: Evidence for a bi-metallic high oxidation state Pd intermediate
    • Deprez, N. R., Sanford, M. S. Synthetic and mechanistic studies of Pd-catalyzed CH arylation with diaryliodonium salts: evidence for a bi-metallic high oxidation state Pd intermediate. J. Am. Chem. Soc. 131, 11234-11241 (2009).
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 11234-11241
    • Deprez, N.R.1    Sanford, M.S.2
  • 29
  • 30
    • 84864218590 scopus 로고    scopus 로고
    • Connecting binuclear Pd(III) and mononuclear Pd(IV) chemistry by PdPd bond cleavage
    • Powers, D. C. et al. Connecting binuclear Pd(III) and mononuclear Pd(IV) chemistry by PdPd bond cleavage. J. Am. Chem. Soc. 134, 12002-12009 (2012).
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 12002-12009
    • Powers, D.C.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.