Silver-catalyzed three-component reaction: synthesis of N~2-substituted 1,2,3-triazoles via direct benzylic amination
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摘要
A novel Ag(Ⅰ)-catalyzed benzylic amination reaction with in situ generation of NH-1,2,3-triazoles for N~2-substituted 1,2,3 triazole scaffolds is described. This protocol is achieved with easily accessible substrate, broad functional group, good re gioselectivity, thus providing the efficient and practical method to diverse N~2-substituted 1,2,3-triazole rings with moderate t good yields.
A novel Ag(Ⅰ)-catalyzed benzylic amination reaction with in situ generation of NH-1,2,3-triazoles for N~2-substituted 1,2,3 triazole scaffolds is described. This protocol is achieved with easily accessible substrate, broad functional group, good re gioselectivity, thus providing the efficient and practical method to diverse N~2-substituted 1,2,3-triazole rings with moderate t good yields.
A novel Ag(Ⅰ)-catalyzed benzylic amination reaction with in situ generation of NH-1,2,3-triazoles for N~2-substituted 1,2,3 triazole scaffolds is described. This protocol is achieved with easily accessible substrate, broad functional group, good re gioselectivity, thus providing the efficient and practical method to diverse N~2-substituted 1,2,3-triazole rings with moderate t good yields.
引文
1(a)Davies HML,Alford JS.Chem Soc Rev,2014,43:5151-5162;(b)Huang D,Zhao P,Astruc D.Coordin Chem Rev,2014,272:145-165;(c)Hosseyni S,Wojtas L,Li M,Shi X.J Am Chem Soc,2016,138:3994-3997;(d)Ye X,Xu C,Wojtas L,Akhmedov NG,Chen H,Shi X.Org Lett,2016,18:2970-2973;(e)Goitia A,Gómez-Bengoa E,Correa A.Org Lett,2017,19:962-965
2(a)Kacprzak K,Skiera I,Piasecka M,Paryzek Z.Chem Rev,2016,116:5689-5743;(b)Kolb HC,Sharpless KB.Drug Discovery Today,2003,8:1128-1137;(c)Whiting M,Tripp JC,Lin YC,Lindstrom W,Olson AJ,Elder JH,Sharpless KB,Fokin VV.J Med Chem,2006,49:7697-7710;(d)Wilkinson BL,Bornaghi LF,Houston TA,Poulsen SA.In:Kaplan S P,ed.Drug Design Research Perspectives.Nova:Haupauge,2007.57;(e)Chrovian CC,Soyode-Johnson A,Peterson AA,Gelin CF,Deng X,Dvorak CA,Carruthers NI,Lord B,Fraser I,Aluisio L,Coe KJ,Scott B,Koudriakova T,Schoetens F,Sepassi K,Gallacher DJ,Bhattacharya A,Letavic MA.J Med Chem,2018,61:207-223
3(a)Zheng Y,Ji X,Yu B,Ji K,Gallo D,Csizmadia E,Zhu M,Choudhury MR,De La Cruz LKC,Chittavong V,Pan Z,Yuan Z,Otterbein LE,Wang B.Nat Chem,2018,10:787-794;(b)Tiwari VK,Mishra BB,Mishra KB,Mishra N,Singh AS,Chen X.Chem Rev,2016,116:3086-3240;(c)Kim WG,Choi B,Yang HJ,Han JA,Jung H,Cho HJ,Kang S,Hong SY.Bioconjugate Chem,2016,27:2007-2013;(d)Thirumurugan P,Matosiuk D,Jozwiak K.Chem Rev,2013,113:4905-4979;(e)Tang W,Becker ML.Chem Soc Rev,2014,43:7013-7039;(f)Tian H,Fürstenberg A,Huber T.Chem Rev,2017,117:186-245
4(a)Finn MG,Fokin VV.Chem Soc Rev,2010,39:1231;(b)Kumar AS,Ghule VD,Subrahmanyam S,Sahoo AK.Chem Eur J,2013,19:509-518;(c)Hawker CJ,Fokin VV,Finn MG,Sharpless KB.Aust JChem,2007,60:381-383;(d)Chu C,Liu R.Chem Soc Rev,2011,40:2177-2188;(e)Astruc D,Liang L,Rapakousiou A,Ruiz J.Acc Chem Res,2012,45:630-640;(f)Leophairatana P,Samanta S,De Silva CC,Koberstein JT.J Am Chem Soc,2017,139:3756-3766
5 Huisgen R.Angew Chem Int Ed Engl,1963,2:565-598
6 Kolb HC,Finn MG,Sharpless KB.Angew Chem Int Ed,2001,40:2004-2021
7(a)Rostovtsev VV,Green LG,Fokin VV,Sharpless KB.Angew Chem Int Ed,2002,41:2596-2599;(b)Torn?e CW,Christensen C,Meldal M.J Org Chem,2002,67:3057-3064
8(a)Fokin VV.In:Ding K,Dai L-X,eds.Organic Chemistry-Breakthroughs and Perspectives.Weinheim:Wiley-VCH,2012.247-277;(b)Banert K.In:Br?se S,Banert K,Eds.Organic Azides:Syntheses and Applications.Chichester:Wiley,2010;(c)Wei F,Wang W,Ma Y,Tung CH,Xu Z.Chem Commun,2016,52:14188-14199;(d)Kappe CO,Van der Eycken E.Chem Soc Rev,2010,39:1280-1290;(e)Johansson JR,Beke-Somfai T,Said St?lsmeden A,Kann N.Chem Rev,2016,116:14726-14768;(f)Wang Z,Li B,Zhang X,Fan X.JOrg Chem,2016,81:6357-6363;(g)Wang Q,Shi X,Zhang X,Fan X.Org Biomol Chem,2017,15:8529-8534
9 Kim WG,Kang ME,Lee JB,Jeon MH,Lee S,Lee J,Choi B,Cal PMSD,Kang S,Kee JM,Bernardes GJL,Rohde JU,Choe W,Hong SY.J Am Chem Soc,2017,139:12121-12124
10(a)Zhu L,Zhang H,Wang C,Chen Z.Chin J Org Chem,2018,38:1052-1064;(b)Chen Y,Liu Y,Petersen JL,Shi X.Chem Commun,2008,2:3254-3256;(c)Kalisiak J,Sharpless KB,Fokin VV.Org Lett,2008,10:3171-3174;(d)Wang XJ,Sidhu K,Zhang L,Campbell S,Haddad N,Reeves DC,Krishnamurthy D,Senanayake CH.Org Lett,2009,11:5490-5493;(e)Wang X,Zhang L,Krishnamurthy D,Senanayake CH,Wipf P.Org Lett,2010,12:4632-4635;(f)Yan W,Wang Q,Chen Y,Petersen JL,Shi X.Org Lett,2010,12:3308-3311;(g)Liu Y,Yan W,Chen Y,Petersen JL,Shi X.Org Lett,2008,10:5389-5392;(h)Zhang Y,Ye X,Petersen JL,Li M,Shi X.J Org Chem,2015,80:3664-3669;(i)Wang X,Zhang L,Lee H,Haddad N,Krishnamurthy D,Senanayake CH.Org Lett,2009,11:5026-5028;(j)Ueda S,Su M,Buchwald SL.Angew Chem Int Ed,2011,50:8944-8947;(k)Ueda S,Ali S,Fors BP,Buchwald SL.J Org Chem,2012,77:2543-2547
11(a)Guru MM,Punniyamurthy T.J Org Chem,2012,77:5063-5073;(b)Stewart S,Harris R,Jamieson C.Synlett,2014,25:2480-2484;(c)Wu L,Guo S,Wang X,Guo Z,Yao G,Lin Q,Wu M.Tetrahedron Lett,2015,56:2145-2148;(d)Gavlik KD,Lesogorova SG,Sukhorukova ES,Subbotina JO,Slepukhin PA,Benassi E,Belskaya NP.Eur J Org Chem,2016,2016:2700-2710;(e)Zhou J,He J,Wang B,Yang W,Ren H.J Am Chem Soc,2011,133:6868-6870;(f)Ryu T,Min J,Choi W,Jeon WH,Lee PH.Org Lett,2014,16:2810-2813;(g)Li J,Zhou H,Zhang J,Yang H,Jiang G.Chem Commun,2016,52:9589-9592
12 Kamijo S,Jin T,Huo Z,Yamamoto Y.J Org Chem,2003,69:2386-2393
13 Kalisiak J,Sharpless KB,Fokin VV.Org Lett,2008,10:3171-3174
14(a)Peshkov VA,Pereshivko OP,Nechaev AA,Peshkov AA,Van der Eycken EV.Chem Soc Rev,2018,47:3861-3898;(b)Boyarskiy VP,Ryabukhin DS,Bokach NA,Vasilyev AV.Chem Rev,2016,116:5894-5986;(c)Yang L,Huang H.Chem Rev,2015,115:3468-3517;(d)Dorel R,Echavarren AM.Chem Rev,2015,115:9028-9072;(e)Asiri AM,Hashmi ASK.Chem Soc Rev,2016,45:4471-4503;(f)Zeng X.Chem Rev,2013,113:6864-6900;(g)Müller DS,Marek I.Chem Soc Rev,2016,45:4552-4566
15(a)Fang G,Bi X.Chem Soc Rev,2015,44:8124-8173;(b)Sekine K,Yamada T.Chem Soc Rev,2016,45:4524-4532;(c)Ning Y,Ji Q,Liao P,Anderson EA,Bi X.Angew Chem Int Ed,2017,56:13805-13808;(d)Sadamitsu Y,Komatsuki K,Saito K,Yamada T.Org Lett,2017,19:3191-3194;(e)Wang H,Mi P,Zhao W,Kumar R,Bi X.Org Lett,2017,19:5613-5616;(f)Liu Z,Li Q,Liao P,Bi X.Chem Eur J,2017,23:4756-4760;(g)Barve IJ,Thikekar TU,Sun CM.Org Lett,2017,19:2370-2373;(h)Tang J,Sivaguru P,Ning Y,Zanoni G,Bi X.Org Lett,2017,19:4026-4029;(i)Liu JQ,Shen X,Wang Y,Wang XS,Bi X.Org Lett,2018,20:6930-6933
16(a)Liu Z,Ji H,Gao W,Zhu G,Tong L,Lei F,Tang B.Chem Commun,2017,53:6259-6262;(b)Xu T,Hu X.Angew Chem Int Ed,2015,54:1307-1311;(c)Shen T,Wang T,Qin C,Jiao N.Angew Chem Int Ed,2013,52:6677-6680
17(a)Meier BW,Gomez JD,Zhou A,Thompson JA.Chem Res Toxicol,2005,18:1575-1585;(b)Lemercier JN,Meier BW,Gomez JD,Thompson JA.Chem Res Toxicol,2004,17:1675-1683;(c)Kupfer R,Dwyer-Nield LD,Malkinson AM,Thompson JA.Chem Res Toxicol,2002,15:1106-1112;(d)Zhou Q,Turnbull KD.J Org Chem,2001,66:7072-7077
18(a)CCDC 1849952 of 3a-N1(b)CCDC 1881654 of 3f-N2(c)CCDC1898986 of 3x(d)CCDC 1881653 of 4h(e)CCDC 1898987 of 4n.All the supplementary crystallographic data for this paper are from Cambridge Crystallographic Data Centre http://www.ccdc.cam.ac.uk/
19 Creary X,Anderson A,Brophy C,Crowell F,Funk Z.J Org Chem,2012,77:8756-8761
20 Jin T,Kamijo S,Yamamoto Y.Eur J Org Chem,2004,2004:3789-3791
21 Vitérisi A,Orsini A,Weibel JM,Pale P.Tetrahedron Lett,2006,47:2779-2781
2(a)Kacprzak K,Skiera I,Piasecka M,Paryzek Z.Chem Rev,2016,116:5689-5743;(b)Kolb HC,Sharpless KB.Drug Discovery Today,2003,8:1128-1137;(c)Whiting M,Tripp JC,Lin YC,Lindstrom W,Olson AJ,Elder JH,Sharpless KB,Fokin VV.J Med Chem,2006,49:7697-7710;(d)Wilkinson BL,Bornaghi LF,Houston TA,Poulsen SA.In:Kaplan S P,ed.Drug Design Research Perspectives.Nova:Haupauge,2007.57;(e)Chrovian CC,Soyode-Johnson A,Peterson AA,Gelin CF,Deng X,Dvorak CA,Carruthers NI,Lord B,Fraser I,Aluisio L,Coe KJ,Scott B,Koudriakova T,Schoetens F,Sepassi K,Gallacher DJ,Bhattacharya A,Letavic MA.J Med Chem,2018,61:207-223
3(a)Zheng Y,Ji X,Yu B,Ji K,Gallo D,Csizmadia E,Zhu M,Choudhury MR,De La Cruz LKC,Chittavong V,Pan Z,Yuan Z,Otterbein LE,Wang B.Nat Chem,2018,10:787-794;(b)Tiwari VK,Mishra BB,Mishra KB,Mishra N,Singh AS,Chen X.Chem Rev,2016,116:3086-3240;(c)Kim WG,Choi B,Yang HJ,Han JA,Jung H,Cho HJ,Kang S,Hong SY.Bioconjugate Chem,2016,27:2007-2013;(d)Thirumurugan P,Matosiuk D,Jozwiak K.Chem Rev,2013,113:4905-4979;(e)Tang W,Becker ML.Chem Soc Rev,2014,43:7013-7039;(f)Tian H,Fürstenberg A,Huber T.Chem Rev,2017,117:186-245
4(a)Finn MG,Fokin VV.Chem Soc Rev,2010,39:1231;(b)Kumar AS,Ghule VD,Subrahmanyam S,Sahoo AK.Chem Eur J,2013,19:509-518;(c)Hawker CJ,Fokin VV,Finn MG,Sharpless KB.Aust JChem,2007,60:381-383;(d)Chu C,Liu R.Chem Soc Rev,2011,40:2177-2188;(e)Astruc D,Liang L,Rapakousiou A,Ruiz J.Acc Chem Res,2012,45:630-640;(f)Leophairatana P,Samanta S,De Silva CC,Koberstein JT.J Am Chem Soc,2017,139:3756-3766
5 Huisgen R.Angew Chem Int Ed Engl,1963,2:565-598
6 Kolb HC,Finn MG,Sharpless KB.Angew Chem Int Ed,2001,40:2004-2021
7(a)Rostovtsev VV,Green LG,Fokin VV,Sharpless KB.Angew Chem Int Ed,2002,41:2596-2599;(b)Torn?e CW,Christensen C,Meldal M.J Org Chem,2002,67:3057-3064
8(a)Fokin VV.In:Ding K,Dai L-X,eds.Organic Chemistry-Breakthroughs and Perspectives.Weinheim:Wiley-VCH,2012.247-277;(b)Banert K.In:Br?se S,Banert K,Eds.Organic Azides:Syntheses and Applications.Chichester:Wiley,2010;(c)Wei F,Wang W,Ma Y,Tung CH,Xu Z.Chem Commun,2016,52:14188-14199;(d)Kappe CO,Van der Eycken E.Chem Soc Rev,2010,39:1280-1290;(e)Johansson JR,Beke-Somfai T,Said St?lsmeden A,Kann N.Chem Rev,2016,116:14726-14768;(f)Wang Z,Li B,Zhang X,Fan X.JOrg Chem,2016,81:6357-6363;(g)Wang Q,Shi X,Zhang X,Fan X.Org Biomol Chem,2017,15:8529-8534
9 Kim WG,Kang ME,Lee JB,Jeon MH,Lee S,Lee J,Choi B,Cal PMSD,Kang S,Kee JM,Bernardes GJL,Rohde JU,Choe W,Hong SY.J Am Chem Soc,2017,139:12121-12124
10(a)Zhu L,Zhang H,Wang C,Chen Z.Chin J Org Chem,2018,38:1052-1064;(b)Chen Y,Liu Y,Petersen JL,Shi X.Chem Commun,2008,2:3254-3256;(c)Kalisiak J,Sharpless KB,Fokin VV.Org Lett,2008,10:3171-3174;(d)Wang XJ,Sidhu K,Zhang L,Campbell S,Haddad N,Reeves DC,Krishnamurthy D,Senanayake CH.Org Lett,2009,11:5490-5493;(e)Wang X,Zhang L,Krishnamurthy D,Senanayake CH,Wipf P.Org Lett,2010,12:4632-4635;(f)Yan W,Wang Q,Chen Y,Petersen JL,Shi X.Org Lett,2010,12:3308-3311;(g)Liu Y,Yan W,Chen Y,Petersen JL,Shi X.Org Lett,2008,10:5389-5392;(h)Zhang Y,Ye X,Petersen JL,Li M,Shi X.J Org Chem,2015,80:3664-3669;(i)Wang X,Zhang L,Lee H,Haddad N,Krishnamurthy D,Senanayake CH.Org Lett,2009,11:5026-5028;(j)Ueda S,Su M,Buchwald SL.Angew Chem Int Ed,2011,50:8944-8947;(k)Ueda S,Ali S,Fors BP,Buchwald SL.J Org Chem,2012,77:2543-2547
11(a)Guru MM,Punniyamurthy T.J Org Chem,2012,77:5063-5073;(b)Stewart S,Harris R,Jamieson C.Synlett,2014,25:2480-2484;(c)Wu L,Guo S,Wang X,Guo Z,Yao G,Lin Q,Wu M.Tetrahedron Lett,2015,56:2145-2148;(d)Gavlik KD,Lesogorova SG,Sukhorukova ES,Subbotina JO,Slepukhin PA,Benassi E,Belskaya NP.Eur J Org Chem,2016,2016:2700-2710;(e)Zhou J,He J,Wang B,Yang W,Ren H.J Am Chem Soc,2011,133:6868-6870;(f)Ryu T,Min J,Choi W,Jeon WH,Lee PH.Org Lett,2014,16:2810-2813;(g)Li J,Zhou H,Zhang J,Yang H,Jiang G.Chem Commun,2016,52:9589-9592
12 Kamijo S,Jin T,Huo Z,Yamamoto Y.J Org Chem,2003,69:2386-2393
13 Kalisiak J,Sharpless KB,Fokin VV.Org Lett,2008,10:3171-3174
14(a)Peshkov VA,Pereshivko OP,Nechaev AA,Peshkov AA,Van der Eycken EV.Chem Soc Rev,2018,47:3861-3898;(b)Boyarskiy VP,Ryabukhin DS,Bokach NA,Vasilyev AV.Chem Rev,2016,116:5894-5986;(c)Yang L,Huang H.Chem Rev,2015,115:3468-3517;(d)Dorel R,Echavarren AM.Chem Rev,2015,115:9028-9072;(e)Asiri AM,Hashmi ASK.Chem Soc Rev,2016,45:4471-4503;(f)Zeng X.Chem Rev,2013,113:6864-6900;(g)Müller DS,Marek I.Chem Soc Rev,2016,45:4552-4566
15(a)Fang G,Bi X.Chem Soc Rev,2015,44:8124-8173;(b)Sekine K,Yamada T.Chem Soc Rev,2016,45:4524-4532;(c)Ning Y,Ji Q,Liao P,Anderson EA,Bi X.Angew Chem Int Ed,2017,56:13805-13808;(d)Sadamitsu Y,Komatsuki K,Saito K,Yamada T.Org Lett,2017,19:3191-3194;(e)Wang H,Mi P,Zhao W,Kumar R,Bi X.Org Lett,2017,19:5613-5616;(f)Liu Z,Li Q,Liao P,Bi X.Chem Eur J,2017,23:4756-4760;(g)Barve IJ,Thikekar TU,Sun CM.Org Lett,2017,19:2370-2373;(h)Tang J,Sivaguru P,Ning Y,Zanoni G,Bi X.Org Lett,2017,19:4026-4029;(i)Liu JQ,Shen X,Wang Y,Wang XS,Bi X.Org Lett,2018,20:6930-6933
16(a)Liu Z,Ji H,Gao W,Zhu G,Tong L,Lei F,Tang B.Chem Commun,2017,53:6259-6262;(b)Xu T,Hu X.Angew Chem Int Ed,2015,54:1307-1311;(c)Shen T,Wang T,Qin C,Jiao N.Angew Chem Int Ed,2013,52:6677-6680
17(a)Meier BW,Gomez JD,Zhou A,Thompson JA.Chem Res Toxicol,2005,18:1575-1585;(b)Lemercier JN,Meier BW,Gomez JD,Thompson JA.Chem Res Toxicol,2004,17:1675-1683;(c)Kupfer R,Dwyer-Nield LD,Malkinson AM,Thompson JA.Chem Res Toxicol,2002,15:1106-1112;(d)Zhou Q,Turnbull KD.J Org Chem,2001,66:7072-7077
18(a)CCDC 1849952 of 3a-N1(b)CCDC 1881654 of 3f-N2(c)CCDC1898986 of 3x(d)CCDC 1881653 of 4h(e)CCDC 1898987 of 4n.All the supplementary crystallographic data for this paper are from Cambridge Crystallographic Data Centre http://www.ccdc.cam.ac.uk/
19 Creary X,Anderson A,Brophy C,Crowell F,Funk Z.J Org Chem,2012,77:8756-8761
20 Jin T,Kamijo S,Yamamoto Y.Eur J Org Chem,2004,2004:3789-3791
21 Vitérisi A,Orsini A,Weibel JM,Pale P.Tetrahedron Lett,2006,47:2779-2781