Organic Letters
Letter
(18) Mukaiyama, T. Angew. Chem., Int. Ed. 2004, 43, 5590.
19) Luo, Q.-L.; Lv, L.; Li, Y.; Tan, J.-P.; Nan, W.; Hui, Q. Eur. J. Org.
Chem. 2011, 2011, 6916.
(
CCDC 1577749 contains the supplementary crystallographic
Crystallographic Data Centre, 12 Union Road, Cambridge CB2
(
20) Kroutil describes the various modes of simultaneous oxidation−
reduction reactions carried out in one pot for biocatalytic oxidation-
reduction cascades. Schrittwieser, J. H.; Sattler, J.; Resch, V.; Mutti, F. G.;
Kroutil, W. Curr. Opin. Chem. Biol. 2011, 15, 249.
1EZ, UK; fax: +44 1223 336033.
(21) Hirose, D.; Gazvoda, M.; Kosmrlj, J.; Taniguchi, T. Org. Lett. 2016,
1
8, 4036.
AUTHOR INFORMATION
(22) But, T. Y.; Toy, P. H. J. Am. Chem. Soc. 2006, 128, 9636.
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23)Hirose,D.;Taniguchi, T.;Ishibashi,H. Angew. Chem., Int.Ed.2013,
2, 4613.
24) Hirose, D.; Gazvoda, M.; Kosm
016, 7, 5148.
25) Buonomo, J. A.; Aldrich, C. C. Angew. Chem., Int. Ed. 2015, 54,
3041.
(26) Lenstra, D. C.; Rutjes, F. P.; Mecinovic, J. Chem. Commun. 2014,
50, 5763.
5
ORCID
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rlj, J.; Taniguchi, T. Chem. Sci.
2
(
1
Present Address
†(
P.G.) Medicinal Chemistry Department, NIPER Hyderabad,
Hyderabad, Telangana 500037, India.
Notes
(27) Taniguchi, T.; Hirose, D.; Ishibashi, H. ACS Catal. 2011, 1, 1469.
(28) Liebeskind, L. S.; Gangireddy, P.; Lindale, M. G. J. Am. Chem. Soc.
2016, 138, 6715.
29)Gangireddy, P.;Patro, V.;Lam, L.;Morimoto, M.;Liebeskind, L. S.
J. Org. Chem. 2017, 82, 3513.
30) The Cu-catalyzed aerobic regeneration of the benzoisothiazolone
(
The authors declare no competing financial interest.
(
ACKNOWLEDGMENTS
This work was supported by the National Science Foundation
CHE-1362281 and CHE-1531620 (NMR Facility)). We
acknowledge the use of the Rigaku SYNERGY diffractometer,
supported by the National Science Foundation (CHE-1626172).
We thank Dr John Bacsa, Emory X-ray Crystallography Facility,
for the X-ray structural analysis. We thank Dr. Nikolai V. Orlov
Moscow) for his early contributions to the project. Dr. Savita K.
Sharma in Dr. Cora MacBeth’s Emory University laboratory
provided assistance with the UV−vis studies.
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from the 2-mercaptobenzamide proceeds through the intermediacy of
the disulfide under our reaction conditions, in contrast to: Wang, Z.;
Kuninobu, Y.; Kanai, M. J. Org. Chem. 2013, 78, 7337. The disulfide
suffers a Cu-catalyzed disproportionation to the benzoisothiazolone.
(31) Reich, H. J.; Hondal, R. J. ACS Chem. Biol. 2016, 11, 821.
(
32)Nauser, T.;Steinmann, D.;Koppenol, W.H. AminoAcids2012,42,
9.
33) Wessjohann, L. A.; Schneider, A.; Abbas, M.; Brandt, W. Biol.
Chem. 2007, 388, 997.
3
(
(
(34) Bhabak, K. P.; Mugesh, G. Acc. Chem. Res. 2010, 43, 1408.
(35) Mugesh, G.; du Mont, W.-W.; Sies, H. Chem. Rev. 2001, 101, 2125.
(36) Some benzoisoselenazolones are highly effective glutathione
DEDICATION
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peroxidase mimics, rapidly reacting with hydroperoxides in the presence
of sacrificial thiol reductants: (a) Bhabak, K. P.; Mugesh, G. Acc. Chem.
Res. 2010, 43, 1408. (b)Mugesh, G.;du Mont, W.-W.;Sies, H. Chem. Rev.
Dedicated to our colleague Professor Dr. Albert Padwa on the
occasion of his 80th birthday.
2
001, 101, 2125. (c) Alberto, E. E.; Nascimento, V. d.; Braga, A. L. J. Braz.
Chem. Soc. 2010, 21, 2032.
37) Astoichiometric redoxdehydration basedon diaryldiselenides and
REFERENCES
■
(
(
1)Chen, Z.;Zeng, H.;Girard, S. A.;Wang, F.;Chen, N.;Li, C. J. Angew.
Chem., Int. Ed. 2015, 54, 14487.
2) An, J.; Denton, R. M.; Lambert, T. H.; Nacsa, E. D. Org. Biomol.
Chem. 2014, 12, 2993.
3)Lundberg, H.;Tinnis, F.;Selander, N.;Adolfsson, H. Chem. Soc. Rev.
014, 43, 2714.
4) Dunn, P. J.; Hii, K. K. M.; Krische, M. J.; Williams, M. T. Sustainable
Catalysis. Challenges and Practices for the Pharmaceutical and Fine
Chemical Industries; John Wiley and Sons: Hoboken, NJ, 2013.
5) Lanigan, R. M.; Sheppard, T. D. Eur. J. Org. Chem. 2013, 2013, 7453.
6) Kumar, R.; Van der Eycken, E. V. Chem. Soc. Rev. 2013, 42, 1121.
7) Hamid, M. H. S. A.; Slatford, P. A.; Williams, J. M. J. Adv. Synth.
tri-n-butylphosphine was described in the 1990s: Singh, U.; Ghosh, S. K.;
Chadha, M. S.; Mamdapur, V. R. Tetrahedron Lett. 1991, 32, 255.
(
(38) The uncatalyzed disproportionation of ortho functionalized
diselenides to benzoisoselenazolones is highly dependent on the nature
of the diselenide: (a) Bhabak, K. P.; Mugesh, G. Acc. Chem. Res. 2010, 43,
(
2
(
1
1
408. (b) Bhowmick, D.; Mugesh, G. Org. Biomol. Chem. 2015, 13,
0262.
(
39) Westheimer, F. H.; Huang, S.; Covitz, F. J. Am. Chem. Soc. 1988,
10, 181.
40) Mlochowski, J.; Wojtowicz-Mlochowska, H. Molecules 2015, 20,
0205.
41) Sancineto, L.; Tidei, C.; Bagnoli, L.; Marini, F.; Lenardao, E. J.;
Santi, C. Molecules 2015, 20, 10496.
42) ten Brink, G.-J.; Fernandes, B. C. M.; van Vliet, M. C. A.; Arends, I.
W. C. E.; Sheldon, R. A. J. Chem. Soc., Perkin Trans. 2001, 1, 224.
43) Van Der Auwera, C.; van Damme, S.; Anteunis, M. Int. J. Pept.
Protein Res. 1987, 29, 464.
44) Miyazawa, T.; Otomatsu, T.; Fukui, T.; Tamada, T.; Kuwata, S. Int.
J. Pept. Protein Res. 1992, 39, 237.
1
(
1
(
(
(
(
Catal. 2007, 349, 1555.
8) Gunanathan, C.; Milstein, D. Science 2013, 341, 1229712.
9) Nixon, T. D.; Whittlesey, M. K.; Williams, J. M. J. Dalton Trans.
(
(
2
(
(
009, 753.
10) Charville, H.; Jackson, D.; Hodges, G.; Whiting, A. Chem.
Commun. 2010, 46, 1813.
11) Krause, T.; Baader, S.; Erb, B.; Goossen, L. J. Nat. Commun. 2016,
, 11732.
12) Zheng, H.; Hall, D. G. Aldrichimica Acta 2014, 47, 41.
13) Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1976, 15, 94.
14) Hughes, D. Org. React. 1992, 42, 335.
(
(
(
7
(
(
(
(
(
(45) Bhowmick, D.; Mugesh, G. Org. Biomol. Chem. 2015, 13, 9072.
15) But, T. Y.; Toy, P. H. Chem. - Asian J. 2007, 2, 1340.
16)Swamy, K. C. K.;Kumar, N. N. B.;Balaraman, E.;Kumar, K. V. P. P.
Chem. Rev. 2009, 109, 2551.
17) Mukaiyama, T.; Kuroda, K.; Maruyama, Y. Heterocycles 2010, 80,
3.
(
6
D
Org. Lett. XXXX, XXX, XXX−XXX