메뉴 건너뛰기




Volumn 516, Issue 7531, 2014, Pages 343-348

Functionalized olefin cross-coupling to construct carbon-carbon bonds

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLAMIDE; ACRYLIC ACID; ALKENE; ALKYL GROUP; BORON; ESTRONE DERIVATIVE; ETHER DERIVATIVE; FUNCTIONAL GROUP; LEWIS ACID; PHENETHYLAMINE; SILANE DERIVATIVE; SULFIDE; VINYL DERIVATIVE; CARBON;

EID: 84922792786     PISSN: 00280836     EISSN: 14764687     Source Type: Journal    
DOI: 10.1038/nature14006     Document Type: Article
Times cited : (345)

References (47)
  • 2
    • 0000038893 scopus 로고
    • A new method for the preparation of alcohols from olefins with molecular oxygen and phenylsilane by the use of bis(acetylacetonato)cobalt(II)
    • Isayama, S. & Mukaiyama, T. A new method for the preparation of alcohols from olefins with molecular oxygen and phenylsilane by the use of bis(acetylacetonato)cobalt(II). Chem. Lett. 18, 1071-1074 (1989).
    • (1989) Chem. Lett. , vol.18 , pp. 1071-1074
    • Isayama, S.1    Mukaiyama, T.2
  • 3
    • 2742609763 scopus 로고
    • Iron(III) complex catalyzed nitrosation of terminal and 1,2-disubstituted olefins with butyl nitrite and phenylsilane
    • Kato, K. & Mukaiyama, T. Iron(III) complex catalyzed nitrosation of terminal and 1,2-disubstituted olefins with butyl nitrite and phenylsilane. Chem. Lett. 21, 1137-1140 (1992).
    • (1992) Chem. Lett. , vol.21 , pp. 1137-1140
    • Kato, K.1    Mukaiyama, T.2
  • 4
    • 33748339796 scopus 로고    scopus 로고
    • Hydrazines and azides via the metal-catalyzed hydrohydrazination and hydroazidation of olefins
    • Waser, J., Gaspar, B., Nambu, H. & Carreira, E. M. Hydrazines and azides via the metal-catalyzed hydrohydrazination and hydroazidation of olefins. J. Am. Chem. Soc. 128, 11693-11712 (2006).
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 11693-11712
    • Waser, J.1    Gaspar, B.2    Nambu, H.3    Carreira, E.M.4
  • 5
    • 84858665556 scopus 로고    scopus 로고
    • Iron(III)/NaBH4-mediated additions to unactivated alkenes: Synthesis of novel 209-vinblastine analogues
    • Leggans, E. K., Barker, T. J., Duncan, K. K. & Boger, D. L. Iron(III)/NaBH4-mediated additions to unactivated alkenes: synthesis of novel 209-vinblastine analogues. Org. Lett. 14, 1428-1431 (2012).
    • (2012) Org. Lett. , vol.14 , pp. 1428-1431
    • Leggans, E.K.1    Barker, T.J.2    Duncan, K.K.3    Boger, D.L.4
  • 6
    • 84880358874 scopus 로고    scopus 로고
    • Hydroalkoxylation of unactivated olefins with carbon radicals and carbocation species as key intermediates
    • Shigehisa, H., Aoki, T., Yamaguchi, S., Shimizu, N.& Hiroya, K. Hydroalkoxylation of unactivated olefins with carbon radicals and carbocation species as key intermediates. J. Am. Chem. Soc. 135, 10306-10309 (2013).
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 10306-10309
    • Shigehisa, H.1    Aoki, T.2    Yamaguchi, S.3    Shimizu, N.4    Hiroya, K.5
  • 7
    • 84886264618 scopus 로고    scopus 로고
    • Cobalt-catalyzedhydrofluorination of unactivated olefins: A radical approach of fluorine transfer
    • Shigehisa, H., Nishi, E.,Fujisawa, M. & Hiroya, K.Cobalt-catalyzedhydrofluorination of unactivated olefins: a radical approach of fluorine transfer. Org. Lett. 15, 5158-5161 (2013).
    • (2013) Org. Lett. , vol.15 , pp. 5158-5161
    • Shigehisa, H.1    Nishi, E.2    Fujisawa, M.3    Hiroya, K.4
  • 8
    • 79961093490 scopus 로고    scopus 로고
    • Regioselective cobalt-catalyzed addition of sulfides to unactivated alkenes
    • Girijavallabhan, V., Alvarez, C. & Njoroge, F. G. Regioselective cobalt-catalyzed addition of sulfides to unactivated alkenes. J. Org. Chem. 76, 6442-6446 (2011).
    • (2011) J. Org. Chem. , vol.76 , pp. 6442-6446
    • Girijavallabhan, V.1    Alvarez, C.2    Njoroge, F.G.3
  • 9
    • 73949140641 scopus 로고    scopus 로고
    • Iron-catalyzed redox radical cyclizations of 1,6-dienes and enynes
    • Taniguchi, T., Goto, N., Nishibata, A. & Ishibashi, H. Iron-catalyzed redox radical cyclizations of 1,6-dienes and enynes. Org. Lett. 12, 112-115 (2010).
    • (2010) Org. Lett. , vol.12 , pp. 112-115
    • Taniguchi, T.1    Goto, N.2    Nishibata, A.3    Ishibashi, H.4
  • 10
    • 0037077589 scopus 로고    scopus 로고
    • Diastereoselective cycloreductions and cycloadditions catalyzed by Co(dpm) 2-silane (dpm) 2, 2,6,6-tetramethylheptane-3,5-dionate): Mechanism and partitioning of hydrometallative versus anion radical pathways
    • Wang, L. C. et al. Diastereoselective cycloreductions and cycloadditions catalyzed by Co(dpm)2-silane (dpm) 2,2,6,6-tetramethylheptane-3,5-dionate): mechanism and partitioning of hydrometallative versus anion radical pathways. J. Am. Chem. Soc. 124, 9448-9453 (2002).
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 9448-9453
    • Wang, L.C.1
  • 11
    • 84872893355 scopus 로고    scopus 로고
    • The electron-way: Metal-catalyzed reductive umpolung reactions of saturated and a,b-unsaturated carbonyl derivatives
    • Streuff, J. The electron-way: metal-catalyzed reductive umpolung reactions of saturated and a,b-unsaturated carbonyl derivatives. Synthesis 45, 281-307 (2013).
    • (2013) Synthesis , vol.45 , pp. 281-307
    • Streuff, J.1
  • 12
    • 84859967678 scopus 로고    scopus 로고
    • Enantioselective C-H crotylation of primary alcohols via hydrohydroxyalkylation of butadiene
    • Zbieg, J. R., Yamaguchi, E., McInturff, E. L. & Krische, M. J. Enantioselective C-H crotylation of primary alcohols via hydrohydroxyalkylation of butadiene. Science 336, 324-327 (2012).
    • (2012) Science , vol.336 , pp. 324-327
    • Zbieg, J.R.1    Yamaguchi, E.2    McInturff, E.L.3    Krische, M.J.4
  • 13
    • 84893467790 scopus 로고    scopus 로고
    • A practical and catalytic reductive olefin coupling
    • Lo, J. C., Yabe, Y. & Baran, P. S. A practical and catalytic reductive olefin coupling. J. Am. Chem. Soc. 136, 1304-1307 (2014).
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 1304-1307
    • Lo, J.C.1    Yabe, Y.2    Baran, P.S.3
  • 14
    • 25844443429 scopus 로고    scopus 로고
    • Advances in radical conjugate additions
    • Srikanth, G. S. C. & Castle, S. L. Advances in radical conjugate additions. Tetrahedron 61, 10377-10441 (2005).
    • (2005) Tetrahedron , vol.61 , pp. 10377-10441
    • Srikanth, G.S.C.1    Castle, S.L.2
  • 15
    • 84886899607 scopus 로고    scopus 로고
    • Direct construction of quaternary carbons from tertiary alcohols via photoredox-catalyzed fragmentation of tertalkyl N-phthalimidoyl oxalates
    • Lackner, G. L., Quasdorf, K. W. & Overman, L. E. Direct construction of quaternary carbons from tertiary alcohols via photoredox-catalyzed fragmentation of tertalkyl N-phthalimidoyl oxalates. J. Am. Chem. Soc. 135, 15342-15345 (2013).
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 15342-15345
    • Lackner, G.L.1    Quasdorf, K.W.2    Overman, L.E.3
  • 16
    • 0001756820 scopus 로고
    • Formation of quaternary carbon centres from tertiary alcohols by free radical methods
    • Barton, D. H. R. & Crich, D. Formation of quaternary carbon centres from tertiary alcohols by free radical methods. Tetrahedron Lett. 26, 757-760 (1985).
    • (1985) Tetrahedron Lett. , vol.26 , pp. 757-760
    • Barton, D.H.R.1    Crich, D.2
  • 17
    • 0001690152 scopus 로고
    • Formation of carbon-carbon bonds with radicals derived from the esters of thiohydroxamic acids
    • Barton, D. H. R., Crich, D. & Kretzchmar, G. Formation of carbon-carbon bonds with radicals derived from the esters of thiohydroxamic acids. Tetrahedron Lett. 25, 1055-1058 (1984).
    • (1984) Tetrahedron Lett. , vol.25 , pp. 1055-1058
    • Barton, D.H.R.1    Crich, D.2    Kretzchmar, G.3
  • 19
    • 84900827256 scopus 로고    scopus 로고
    • A method for the selective hydrogenation of alkenyl halides to alkyl halides
    • King, S. M., Ma, X. & Herzon, S. B. A method for the selective hydrogenation of alkenyl halides to alkyl halides. J. Am. Chem. Soc. 136, 6884-6887 (2014).
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 6884-6887
    • King, S.M.1    Ma, X.2    Herzon, S.B.3
  • 20
    • 0034627368 scopus 로고    scopus 로고
    • Conjugate reduction of a,b-unsaturated ketones using an MnIII catalyst, phenylsilane and isopropyl alcohol
    • Magnus, P., Waring, M. J. & Scott, D. A. Conjugate reduction of a,b-unsaturated ketones using an MnIII catalyst, phenylsilane and isopropyl alcohol. Tetrahedron Lett. 41, 9731-9733 (2000).
    • (2000) Tetrahedron Lett. , vol.41 , pp. 9731-9733
    • Magnus, P.1    Waring, M.J.2    Scott, D.A.3
  • 21
    • 78649862346 scopus 로고    scopus 로고
    • FeCl3-catalyzed addition of nitrogen and 1,3-dicarbonyl nucleophiles to olefins
    • Zotto, C. D. et al. FeCl3-catalyzed addition of nitrogen and 1,3-dicarbonyl nucleophiles to olefins. J. Organomet. Chem. 696, 296-304 (2011).
    • (2011) J. Organomet. Chem. , vol.696 , pp. 296-304
    • Zotto, C.D.1
  • 23
    • 0000458625 scopus 로고
    • Steroids. LIV Synthesis of 19-nor-17a-ethynyltestosterone and 19-nor-17amethyltestosterone
    • Djerassi, C., Miramontes, L., Rosenkranz, G. & Sondheimer, F. Steroids. LIV. Synthesis of 19-nor-17a-ethynyltestosterone and 19-nor-17amethyltestosterone. J. Am. Chem. Soc. 76, 4092-4094 (1954).
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 4092-4094
    • Djerassi, C.1    Miramontes, L.2    Rosenkranz, G.3    Sondheimer, F.4
  • 24
    • 0033516455 scopus 로고    scopus 로고
    • Recent applications of a-phenylethylamine (a-PEA) in the preparation of enantiopure compounds. Part 3: A-PEA as chiral auxiliary. Part 4: A-PEA as chiral reagent in the stereodifferentiation of prochiral substrates
    • Juaristi, E., León-Romo, J. L., Reyes, A. & Escalante, J. Recent applications of a-phenylethylamine (a-PEA) in the preparation of enantiopure compounds. Part 3: a-PEA as chiral auxiliary. Part 4: a-PEA as chiral reagent in the stereodifferentiation of prochiral substrates. Tetrahedron Asymmetry 10, 2441-2495 (1999).
    • (1999) Tetrahedron Asymmetry , vol.10 , pp. 2441-2495
    • Juaristi, E.1    León-Romo, J.L.2    Reyes, A.3    Escalante, J.4
  • 25
    • 0002594370 scopus 로고
    • New bicyclic organylboronic esters derived from iminodiacetic acids
    • Mancilla, T. & Contreras, R. New bicyclic organylboronic esters derived from iminodiacetic acids. J. Organomet. Chem. 307, 1-6 (1986).
    • (1986) J. Organomet. Chem. , vol.307 , pp. 1-6
    • Mancilla, T.1    Contreras, R.2
  • 26
    • 34249828956 scopus 로고    scopus 로고
    • A simple and modular strategy for small molecule synthesis: Iterative Suzuki2Miyaura coupling of B-protected haloboronic acid building blocks
    • Gillis, E. P. & Burke, M. D. A simple and modular strategy for small molecule synthesis: iterative Suzuki2Miyaura coupling of B-protected haloboronic acid building blocks. J. Am. Chem. Soc. 129, 6716-6717 (2007).
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 6716-6717
    • Gillis, E.P.1    Burke, M.D.2
  • 27
    • 33846588529 scopus 로고    scopus 로고
    • Boron-masking strategy for the synthesis of oligioarenes via iterative Suzuki-Miyaura coupling
    • Noguchi, H., Hojo, K. & Suginome, M. Boron-masking strategy for the synthesis of oligioarenes via iterative Suzuki-Miyaura coupling. J. Am. Chem. Soc. 129, 758-759 (2007).
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 758-759
    • Noguchi, H.1    Hojo, K.2    Suginome, M.3
  • 28
    • 0000997257 scopus 로고
    • RCuNBF3. 3. Conjugate addition to previously unreactive substituted enoate esters and enoic acids
    • Yamamoto, Y. & Maruyama, K. RCuNBF3. 3. Conjugate addition to previously unreactive substituted enoate esters and enoic acids. J. Am. Chem. Soc. 100, 3240-3241 (1978).
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 3240-3241
    • Yamamoto, Y.1    Maruyama, K.2
  • 29
    • 0033555871 scopus 로고    scopus 로고
    • Conjugate addition of organolithium reagents to a,b-unsaturated carboxylic acids
    • Aurell, M. J., Domingo, L. R., Mestres, R., Munõz, E. & Zaragová, R. J. Conjugate addition of organolithium reagents to a,b-unsaturated carboxylic acids. Tetrahedron 55, 815-830 (1999).
    • (1999) Tetrahedron , vol.55 , pp. 815-830
    • Aurell, M.J.1    Domingo, L.R.2    Mestres, R.3    Munõz, E.4    Zaragová, R.J.5
  • 30
    • 0001376437 scopus 로고
    • Ameliorationof the conjugate additionchemistry of a-alkoxycopper reagents: Application to the stereospecific synthesis of C-glycosides
    • Hutchinson, D. K. & Fuchs, P. L.Ameliorationof the conjugate additionchemistry of a-alkoxycopper reagents: application to the stereospecific synthesis of C-glycosides. J. Am. Chem. Soc. 109, 4930-4939 (1987).
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 4930-4939
    • Hutchinson, D.K.1    Fuchs, P.L.2
  • 32
    • 0348109450 scopus 로고    scopus 로고
    • The growing impact of click chemistry on drug discovery
    • Kolb, H. C. & Sharpless, K. B. The growing impact of click chemistry on drug discovery. Drug Discov. Today 8, 1128-1137 (2003).
    • (2003) Drug Discov. Today , vol.8 , pp. 1128-1137
    • Kolb, H.C.1    Sharpless, K.B.2
  • 33
    • 84905674432 scopus 로고    scopus 로고
    • Carboxylic acids as a traceless activation group for conjugate additions: A three-step synthesis of (6)-pregabalin
    • Chu, L., Ohta, C., Zuo, Z. & MacMillan, D. W. C. Carboxylic acids as a traceless activation group for conjugate additions: a three-step synthesis of (6)-pregabalin. J. Am. Chem. Soc. 136, 10886-10889 (2014).
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 10886-10889
    • Chu, L.1    Ohta, C.2    Zuo, Z.3    MacMillan, D.W.C.4
  • 34
    • 67949110944 scopus 로고    scopus 로고
    • Total synthesis of vinblastine, vincristine, related natural products, and key structural analogs
    • Ishikawa, H. et al. Total synthesis of vinblastine, vincristine, related natural products, and key structural analogs. J. Am. Chem. Soc. 131, 4904-4916 (2009).
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 4904-4916
    • Ishikawa, H.1
  • 35
    • 0000593804 scopus 로고
    • Hydrogen atomtransfer reactions of transition-metal hydrides. Kinetics and mechanism of the hydrogenation of a-cyclopropylstyrene by metal carbonyl hydrides
    • Bullock, R. M. & Samsel, E. G. Hydrogen atomtransfer reactions of transition-metal hydrides. Kinetics and mechanism of the hydrogenation of a-cyclopropylstyrene by metal carbonyl hydrides. J. Am. Chem. Soc. 112, 6886-6898 (1990).
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6886-6898
    • Bullock, R.M.1    Samsel, E.G.2
  • 36
    • 84882976844 scopus 로고    scopus 로고
    • The Mukaiyama aldol reaction: 40 years of continuous development
    • Matsuo, J. & Murakami, M. The Mukaiyama aldol reaction: 40 years of continuous development. Angew. Chem. Int. Edn 52, 9109-9118 (2013).
    • (2013) Angew. Chem. Int. Edn , vol.52 , pp. 9109-9118
    • Matsuo, J.1    Murakami, M.2
  • 38
    • 2042507954 scopus 로고
    • Palladium-catalyzed cross-coupling reactions of organoboron compounds
    • Miyaura, N. & Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 95, 2457-2483 (1995).
    • (1995) Chem. Rev. , vol.95 , pp. 2457-2483
    • Miyaura, N.1    Suzuki, A.2
  • 39
    • 79952656192 scopus 로고    scopus 로고
    • Advances in transition metal (Pd,Ni,Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners
    • Jana, R., Pathak, T. P. & Sigman, M. S. Advances in transition metal (Pd,Ni,Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners. Chem. Rev. 111, 1417-1492 (2011).
    • (2011) Chem. Rev. , vol.111 , pp. 1417-1492
    • Jana, R.1    Pathak, T.P.2    Sigman, M.S.3
  • 40
    • 28744458623 scopus 로고    scopus 로고
    • Organosulfur compounds: Electrophilic reagents in transition-metal-catalyzed carbon-carbon bond-forming reactions
    • Dubbaka, S. R. & Vogel, P. Organosulfur compounds: electrophilic reagents in transition-metal-catalyzed carbon-carbon bond-forming reactions. Angew. Chem. Int. Edn 44, 7674-7684 (2005).
    • (2005) Angew. Chem. Int. Edn , vol.44 , pp. 7674-7684
    • Dubbaka, S.R.1    Vogel, P.2
  • 41
    • 33845373996 scopus 로고
    • Vinylsilane-and alkynylsilane-terminated cyclization reactions
    • Blumenkopf, T. A. & Overman, L. E. Vinylsilane-and alkynylsilane-terminated cyclization reactions. Chem. Rev. 86, 857-873 (1986).
    • (1986) Chem. Rev. , vol.86 , pp. 857-873
    • Blumenkopf, T.A.1    Overman, L.E.2
  • 42
    • 80055021902 scopus 로고    scopus 로고
    • Silicon-based cross-coupling reaction: An environmentally benign version
    • Nakao, Y. & Hiyama, T. Silicon-based cross-coupling reaction: an environmentally benign version. Chem. Soc. Rev. 40, 4893-4901 (2011).
    • (2011) Chem. Soc. Rev. , vol.40 , pp. 4893-4901
    • Nakao, Y.1    Hiyama, T.2
  • 44
    • 0018454939 scopus 로고
    • Methods of reactivity umpolung
    • Seebach, D. Methods of reactivity umpolung. Angew. Chem. Int. Edn Engl. 18, 239-258 (1979).
    • (1979) Angew. Chem. Int. Edn Engl. , vol.18 , pp. 239-258
    • Seebach, D.1
  • 45
    • 84875471131 scopus 로고    scopus 로고
    • Total synthesis of 6-deoxyerythronolideBviaC2C bond-forming transfer hydrogenation
    • Gao, X., Soo, S. K. & Krische, M. J. Total synthesis of 6-deoxyerythronolideBviaC2C bond-forming transfer hydrogenation. J.Am. Chem. Soc. 135, 4223-4226 (2013).
    • (2013) J.Am. Chem. Soc. , vol.135 , pp. 4223-4226
    • Gao, X.1    Soo, S.K.2    Krische, M.J.3
  • 46
    • 84871083602 scopus 로고    scopus 로고
    • Enantioselective Heck arylations of acyclic alkenyl alcohols using a redox-relay strategy
    • Werner, E. W., Mei, T.-S., Burckle, A. J. & Sigman, M. S. Enantioselective Heck arylations of acyclic alkenyl alcohols using a redox-relay strategy. Science 338, 1455-1458 (2012).
    • (2012) Science , vol.338 , pp. 1455-1458
    • Werner, E.W.1    Mei, T.-S.2    Burckle, A.J.3    Sigman, M.S.4
  • 47
    • 79953031273 scopus 로고    scopus 로고
    • Catalytic Z-selective olefin cross-metathesis for natural product synthesis
    • Meek, S. J., O'Brien, R. V., Llaveria, J., Schrock, R. J. & Hoveyda, A. H. Catalytic Z-selective olefin cross-metathesis for natural product synthesis. Nature 471, 461-466 (2011).
    • (2011) Nature , vol.471 , pp. 461-466
    • Meek, S.J.1    O'Brien, R.V.2    Llaveria, J.3    Schrock, R.J.4    Hoveyda, A.H.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.