Ruthenium(ii)-catalyzed switchable C3-alkylation versus alkenylation with acrylates of 2-pyridylbenzofurans via C–H bond activation

Catalysis Science and Technology - Tập 5 Số 1 - Trang 114-117
Yadagiri Kommagalla1,2,3,4, Venkannababu Mullapudi1,2,3,4, Fredi Francis1,2,3,4, Chepuri V. Ramana1,2,3,4
1CSIR-National Chemical Laboratory
2Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411008, India
3India
4Pune-411008

Tóm tắt

We documented an interesting observation of ruthenium(ii)-catalyzed benzofuran C–H activation and subsequent functionalization with acrylates that reveals that a simple base can switch the process from alkylation to alkenylation.

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Tài liệu tham khảo

Culkin, 2003, Acc. Chem. Res., 36, 234, 10.1021/ar0201106

Bellina, 2010, Chem. Rev., 110, 1082, 10.1021/cr9000836

Zhang, 2011, Chem. Soc. Rev., 40, 1937, 10.1039/c0cs00063a

Labinger, 2002, Nature, 417, 507, 10.1038/417507a

Ritleng, 2002, Chem. Rev., 102, 1731, 10.1021/cr0104330

Murai, 1993, Nature, 366, 529, 10.1038/366529a0

Chen, 2009, Angew. Chem., Int. Ed., 48, 5094, 10.1002/anie.200806273

Ackermann, 2011, Chem. Rev., 111, 1315, 10.1021/cr100412j

Colby, 2012, Acc. Chem. Res., 45, 814, 10.1021/ar200190g

Arockiam, 2012, Chem. Rev., 112, 5879, 10.1021/cr300153j

Rouquet, 2013, Angew. Chem., Int. Ed., 52, 11726, 10.1002/anie.201301451

Wencel-Delord, 2011, Chem. Soc. Rev., 40, 4740, 10.1039/c1cs15083a

Kakiuchi, 1995, Bull. Chem. Soc. Jpn., 68, 62, 10.1246/bcsj.68.62

Kommagalla, 2014, Chem. – Eur. J., 20, 7884, 10.1002/chem.201400401

Rouquet, 2013, Chem. Sci., 4, 2201, 10.1039/c3sc50310k

Ueyama, 2011, Org. Lett., 13, 706, 10.1021/ol102942w

Ackermann, 2011, Org. Lett., 13, 4153, 10.1021/ol201563r

Arockiam, 2011, Green Chem., 13, 3075, 10.1039/c1gc15875a

Padala, 2011, Org. Lett., 13, 6144, 10.1021/ol202580e

Lanke, 2013, Org. Lett., 15, 2818, 10.1021/ol4011486

L. D. Quin and J. A.Tyrell, Fundamentals of Heterocyclic Chemistry: Importance in Nature and in the Synthesis of Pharmaceuticals, Wiley, New Jersey, 2007, p. 196

Zeni, 2006, Chem. Rev., 106, 4644, 10.1021/cr0683966

Stuppner, 2011, J. Nat. Prod., 74, 1779, 10.1021/np200343t

Zareba, 2006, Drugs Today, 42, 75, 10.1358/dot.2006.42.2.925346

Rossi, 2014, Adv. Synth. Catal., 356, 17, 10.1002/adsc.201300922

Anwar, 2013, Chem. – Eur. J., 19, 4344, 10.1002/chem.201204221

Carrer, 2012, J. Org. Chem., 77, 1316, 10.1021/jo202060k

Ono, 2011, J. Med. Chem., 54, 2971, 10.1021/jm200057u

Swahn, 2010, Bioorg. Med. Chem. Lett., 20, 1976, 10.1016/j.bmcl.2010.01.105

Zhao, 2013, Asian J. Org. Chem., 2, 1044, 10.1002/ajoc.201300208

Tang, 2013, Comput. Theor. Chem., 1007, 31, 10.1016/j.comptc.2012.10.025

Kuznetsov, 2006, J. Am. Chem. Soc., 128, 14388, 10.1021/ja065249g

M. Beller , A.Zapf and T. H.Riermeier, in Transition Metals for Organic Synthesis, ed. M. Beller and B. Carsten, Wiley-VCH, Weinheim, 2004, vol. 1, p. 271

Heck, 1972, J. Org. Chem., 37, 2320, 10.1021/jo00979a024

Knowles, 2007, Org. Biomol. Chem., 5, 31, 10.1039/B611547K

Pozgan, 2009, Adv. Synth. Catal., 351, 1737, 10.1002/adsc.200900350

Arockiam, 2009, Green Chem., 11, 1871, 10.1039/b913115a

Li, 2012, Tetrahedron, 68, 5179, 10.1016/j.tet.2012.03.117

Li, 2012, Dalton Trans., 41, 10934, 10.1039/c2dt31401k

Flegeau, 2011, J. Am. Chem. Soc., 133, 10161, 10.1021/ja201462n

The exclusive alkylation that resulted in the case of styrene (even in the presence of base) indicates the possible synergistic assistance of the carboxylate group either in stabilizing the alkylruthenium intermediate resulting from the coordinative insertion or the deprotonation of the syn-hydrogen