Abstract
Oxidations with tert-butyl hydroperoxide (TBHP) catalyzed by dirhodium caprolactamate [Rh2(cap)4] provide mild and selective protocols for the oxidative Mannich reaction, conversion of secondary amines to imines, dearomatization of 4-substituted phenols, and oxyfunctionalization of allylic, benzylic, and propargylic positions. The dirhodium catalyst in combination with TBHP is a convenient platform for mechanistic investigations, and their uses point to a variety of directions for the future evolution of the field.
References
1.
M. O. Ratnikov and M. P. Doyle, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2012, DOI: 10.1002/047084289X.r385.
2.
10.1016/j.mencom.2014.06.001_bib0010
Baeckvall
Modern Oxidation Methods,
2011
3.
Forman H.J., Maiorino M., Ursini F.
Biochemistry,
2010
4.
Meunier B., de Visser S.P., Shaik S.
Chemical Reviews,
2004
5.
Mallat T., Baiker A.
Chemical Reviews,
2004
6.
Punniyamurthy T., Velusamy S., Iqbal J.
Chemical Reviews,
2005
7.
S. S. Stahl, Angew. Chem. Int. Ed., 2004, 43, 3400.
8.
Lewis E.A., Tolman W.B.
Chemical Reviews,
2004
9.
Li C.
Accounts of Chemical Research,
2008
10.
Ratnikov M.O., Xu X., Doyle M.P.
Journal of the American Chemical Society,
2013
11.
Ratnikov M.O., Doyle M.P.
Journal of the American Chemical Society,
2013
12.
Catino A.J., Forslund R.E., Doyle M.P.
Journal of the American Chemical Society,
2004
13.
Wang Z., Gao L., Xiong S., Wan C.
Synlett,
2013
14.
Brégeault J.
Dalton Transactions,
2003
15.
Avila D.V., Ingold K.U., Lusztyk J., Green W.H., Procopio D.R.
Journal of the American Chemical Society,
1995
16.
J. Wang, C. Liu, J. Yuan and A. Lei, Angew. Chem. Int. Ed., 2013, 52, 2256.
17.
Schweitzer-Chaput B., Sud A., Pintér Á., Dehn S., Schulze P., Klussmann M.
Angewandte Chemie - International Edition,
2013
18.
Villalobos L., Barker Paredes J.E., Cao Z., Ren T.
Inorganic Chemistry,
2013
19.
Li Y., Ma L., Jia F., Li Z.
Journal of Organic Chemistry,
2013
20.
Sun M., Zhang T., Bao W.
Journal of Organic Chemistry,
2013
21.
Yang B., Yang T., Li X., Wang J., Yang S.
Organic Letters,
2013
22.
Sakai N., Mutsuro A., Ikeda R., Konakahara T.
Synlett,
2013
23.
Qin Z., Xiao Y., Han X., Zhou Z., Wan C.
Synthesis,
2013
24.
Baptistella L.H., Sousa I.M., Gushikem Y., Aleixo A.M.
Tetrahedron Letters,
1999
25.
Shing T.K., Yeung, Su P.L.
Organic Letters,
2006
26.
Miller R.A., Li W., Humphrey G.R.
Tetrahedron Letters,
1996
27.
Yu J., Corey E.J.
Journal of the American Chemical Society,
2003
28.
Zhang S., Guo L., Wang H., Duan X.
Organic and Biomolecular Chemistry,
2013
29.
Cai Z., Wang S., Ji S.
Organic Letters,
2013
30.
Salvador J.A., Silvestre S.M.
Tetrahedron Letters,
2005
31.
Marwah P., Marwah A., Lardy H.A.
Green Chemistry,
2004
32.
Silvestre S.M., Salvador J.A.
Tetrahedron,
2007
33.
Kumar R.A., Saidulu G., Sridhar B., Liu S.T., Reddy K.R.
Journal of Organic Chemistry,
2013
34.
Ratnikov M.O., Farkas L.E., McLaughlin E.C., Chiou G., Choi H., El-Khalafy S.H., Doyle M.P.
Journal of Organic Chemistry,
2011
35.
Uyanik M., Okamoto H., Yasui T., Ishihara K.
Science,
2010
36.
Lu X., Liu Y., Sun B., Cindric B., Deng L.
Journal of the American Chemical Society,
2008
37.
Wu W., Su W.
Journal of the American Chemical Society,
2011
38.
Tian J., Loh T.
Chemical Communications,
2011
39.
Jiang H., Huang H., Cao H., Qi C.
Organic Letters,
2010
40.
Chen S., Xu Y., Wan X.
Organic Letters,
2011
41.
A. Blanc and F. D. Toste, Angew. Chem. Int. Ed., 2006, 45, 2096.
42.
Davies I.R., Cheeseman M., Green R., Mahon M.F., Merritt A., Bull S.D.
Organic Letters,
2009
43.
Weiß K.M., Wei S., Tsogoeva S.B.
Organic and Biomolecular Chemistry,
2011
44.
Efficient and selective epoxidation of styrene with TBHP catalyzed by Au25clusters on hydroxyapatite
Liu Y., Tsunoyama H., Akita T., Tsukuda T.
Chemical Communications,
2010
45.
Michel B.W., Camelio A.M., Cornell C.N., Sigman M.S.
Journal of the American Chemical Society,
2009
46.
B. W. Michel, J. R. McCombs, A. Winkler and M. S. Sigman, Angew. Chem. Int. Ed., 2010, 49, 7312.
47.
Yoo W., Li C.
Journal of the American Chemical Society,
2006
48.
Ji Y., Brueckl T., Baxter R.D., Fujiwara Y., Seiple I.B., Su S., Blackmond D.G., Baran P.S.
Proceedings of the National Academy of Sciences of the United States of America,
2011
49.
W. Zheng, L. Wojtas and J. C. Antilla, Angew. Chem. Int. Ed., 2010, 49, 6589.
50.
Baj S., Chrobok A., Derfla S.
Green Chemistry,
2006
51.
Liu W., Li Y., Liu K., Li Z.
Journal of the American Chemical Society,
2011
52.
Guinaudeau A., Mazières S., Wilson D.J., Destarac M.
Polymer Chemistry,
2012
53.
Tanaka N., Sato E., Matsumoto A.
Organic and Biomolecular Chemistry,
2011
54.
McLaughlin E.C., Choi H., Wang K., Chiou G., Doyle M.P.
Journal of Organic Chemistry,
2008
55.
Choi H., Doyle M.P.
Organic Letters,
2007
56.
57.
Catino A.J., Nichols J.M., Choi H., Gottipamula S., Doyle M.P.
Organic Letters,
2005
58.
McLaughlin E.C., Doyle M.P.
Journal of Organic Chemistry,
2008
59.
Catino A.J., Nichols J.M., Nettles B.J., Doyle M.P.
Journal of the American Chemical Society,
2006
60.
Choi H., Doyle M.P.
Chemical Communications,
2007
61.
Tandem Sequence of Phenol Oxidation and Intramolecular Addition as a Method in Building Heterocycles
Ratnikov M.O., Farkas L.E., Doyle M.P.
Journal of Organic Chemistry,
2012
62.
Lu C., Tusun X.
Synlett,
2012
63.
Wang H., Lu C.
Tetrahedron Letters,
2013
64.
Parish E.J., Kizito S.A., Qiu Z.
Lipids,
2004
65.
KOTANI E., TAKEYA T., EGAWA H., TOBINAGA S.
Chemical and Pharmaceutical Bulletin,
2011
66.
Arsenou E.S., Koutsourea A.I., Fousteris M.A., Nikolaropoulos S.S.
Steroids,
2003
67.
Salvador J.A., Sáe Melo M.L., Campos Neves A.S.
Tetrahedron Letters,
1997
68.
Salvador J.A., Clark J.H.
Chemical Communications,
2001
69.
Enantiomer Recognition of Amides by Dirhodium(II) Tetrakis[methyl 2-oxopyrrolidine-5(S)-carboxylate]
Xu X., Doyle M.P.
Inorganic Chemistry,
2011
70.
Doyle M.P., Ren T.
Progress in Inorganic Chemistry,
2001
71.
10.1016/j.mencom.2014.06.001_bib0355
Doyle
Org. React.,
2013
72.
Doyle M.P., Duffy R., Ratnikov M., Zhou L.
Chemical Reviews,
2009
73.
López I., Rodríguez S., Izquierdo J., González F.V.
Journal of Organic Chemistry,
2007
74.
75.
Russo A., Lattanzi A.
Organic and Biomolecular Chemistry,
2010
76.
De Fusco C., Tedesco C., Lattanzi A.
Journal of Organic Chemistry,
2010
77.
Lv J., Wang X., Liu J., Zhang L., Wang Y.
Tetrahedron Asymmetry,
2006
78.
Russell G.A.
Journal of the American Chemical Society,
1957
79.
Caudle M.T., Riggs-Gelasco P., Gelasco A.K., Penner-Hahn J.E., Pecoraro V.L.
Inorganic Chemistry,
1996
80.
Xiang J., Yuan Y., Guo S.
Synlett,
2013
81.
Deng J., Hsung R.P., Ko C.
Organic Letters,
2012
82.
Hayashi Y., Yamaguchi J., Hibino K., Sumiya T., Urushima T., Shoji M., Hashizume D., Koshino H.
Advanced Synthesis and Catalysis,
2004
83.
Hudlicky T., Rinner U., Gonzalez D., Akgun H., Schilling S., Siengalewicz P., Martinot T.A., Pettit G.R.
Journal of Organic Chemistry,
2002
84.
Abe H., Aoyagi S., Kibayashi C.
Journal of the American Chemical Society,
2000
85.
Villa C., Baldassari S., Gambaro R., Mariani E., Loupy A.
International Journal of Cosmetic Science,
2005
86.
Mizuba S., Sheikh W.
Journal of Industrial Microbiology and Biotechnology,
1987
87.
Wenderski T.A., Huang S., Pettus T.R.
Journal of Organic Chemistry,
2009
88.
Tian J., Zhao Q., Zhang H., Lin Z., Sun H.
Journal of Natural Products,
1997
89.
Chen Y., Shen Y., Su Y., Kong L., Zhang W.
Chemistry and Biodiversity,
2009
90.
Yang H., Hou A., Mei S., Sun H., Che C.
Journal of Asian Natural Products Research,
2002
91.
Hase T., Kawamoto Y., Ohtani K., Kasai R., Yamasaki K., Picheansoonthon C.
Phytochemistry,
1995
92.
Gu Q., Rong Z., Zheng C., You S.
Journal of the American Chemical Society,
2010
93.
You Z., Hoveyda A., Snapper M.
Angewandte Chemie - International Edition,
2009
94.
Lu C., Tusun X.
Synlett,
2013
95.
Snelgrove D.W., Lusztyk J., Banks J.T., Mulder P., Ingold K.U.
Journal of the American Chemical Society,
2000
96.
MacFaul P.A., Arends I.W., Ingold K.U., Wayner D.D.
Journal of the Chemical Society Perkin Transactions 2,
1997
97.
Murahashi S., Naota T., Miyaguchi N., Noda S.
Journal of the American Chemical Society,
1996
98.
Bravo A., Bjørsvik H., Fontana F., Liguori L., Minisci F.
Journal of Organic Chemistry,
1997
99.
Koola J.D., Kochi J.K.
Journal of Organic Chemistry,
1987
100.
Srinivasan K., Perrier S., Kochi J.K.
Journal of Molecular Catalysis,
1986
101.
Chavez F.A., Mascharak P.K.
Accounts of Chemical Research,
2000
102.
Xu L., Korade Z., Porter N.A.
Journal of the American Chemical Society,
2010
103.
Xu L., Davis T.A., Porter N.A.
Journal of the American Chemical Society,
2009
104.
Tallman K.A., Rector C.L., Porter N.A.
Journal of the American Chemical Society,
2009
105.
Kitaguchi H., Ohkubo K., Ogo S., Fukuzumi S.
Journal of the American Chemical Society,
2005
106.
Tallman K.A., Roschek B., Porter N.A.
Journal of the American Chemical Society,
2004
107.
Miyamoto S., Martinez G.R., Medeiros M.H., Di Mascio P.
Journal of the American Chemical Society,
2003
108.
Bozzelli J.W., Sheng C.
Journal of Physical Chemistry A,
2002
109.
Goto Y., Watanabe Y., Fukuzumi S., Jones J.P., Dinnocenzo J.P.
Journal of the American Chemical Society,
1998
110.
Murahashi S., Komiya N.
2010
111.
Murahashi S., Zhang D.
Chemical Society Reviews,
2008
112.
Murahashi S., Naota T., Kuwabara T., Saito T., Kumobayashi H., Akutagawa S.
Journal of the American Chemical Society,
1990
113.
Murahashi S., Naota T., Yonemura K.
Journal of the American Chemical Society,
1988
114.
Wang M., Zhou C., Wong M., Che C.
Chemistry - A European Journal,
2010
115.
Doyle M.P., Timmons D.J., Tumonis J.S., Gau H., Blossey E.C.
Organometallics,
2002
116.
Candeias N.R., Afonso C.A., Gois P.M.
Organic and Biomolecular Chemistry,
2012
117.
Murahashi S., Fujii A., Inubushi Y., Komiya N.
Tetrahedron Letters,
2010
118.
Zheng X., Lu S., Li Z.
Organic Letters,
2013
119.
Wei W., Zhang C., Xu Y., Wan X.
Chemical Communications,
2011