Direct C–H alkylation and indole formation of anilines with diazo compounds under rhodium catalysis

Chemical Communications - Tập 51 Số 97 - Trang 17229-17232
Neeraj Kumar Mishra1,2,3,4, Miji Choi1,2,3,4, Hyeim Jo1,2,3,4, Yongguk Oh1,2,3,4, Satyasheel Sharma1,2,3,4, Sang Hoon Han1,2,3,4, Taejoo Jeong1,2,3,4, Sangil Han1,2,3,4, Seok‐Yong Lee1,2,3,4, In Su Kim1,2,3,4
1Republic of Korea
2School of Pharmacy, Sungkyunkwan University, Suwon 440-746, Republic of Korea
3 SungKyunKwan University
4Suwon 440-746

Tóm tắt

The rhodium(iii)-catalyzed direct functionalization of aniline C–H bonds with α-diazo compounds for the preparation of ortho-alkylated anilines and highly substituted indoles is described.

Từ khóa


Tài liệu tham khảo

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

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

Baudoin, 2011, Chem. Soc. Rev., 40, 4902, 10.1039/c1cs15058h

Kuhl, 2012, Angew. Chem., Int. Ed., 51, 10236, 10.1002/anie.201203269

Mousseau, 2013, Acc. Chem. Res., 46, 412, 10.1021/ar300185z

Chan, 2012, J. Am. Chem. Soc., 134, 13565, 10.1021/ja305771y

Yao, 2012, Angew. Chem., Int. Ed., 51, 775, 10.1002/anie.201106825

Hyster, 2013, J. Am. Chem. Soc., 135, 5364, 10.1021/ja402274g

Shi, 2013, J. Am. Chem. Soc., 135, 12204, 10.1021/ja406338r

Cui, 2013, Chem. Sci., 4, 3912, 10.1039/c3sc51777b

Liang, 2014, Chem. Commun., 50, 6130, 10.1039/C4CC01520G

Zhao, 2015, Angew. Chem., Int. Ed., 54, 4508, 10.1002/anie.201411994

Son, 2015, Org. Lett., 17, 2518, 10.1021/acs.orglett.5b01052

Sharma, 2015, Org. Lett., 17, 2852, 10.1021/acs.orglett.5b01298

Hu, 2014, Angew. Chem., Int. Ed., 53, 1364, 10.1002/anie.201309650

Xu, 2015, Angew. Chem., Int. Ed., 54, 4669, 10.1002/anie.201412450

Yu, 2013, J. Org. Chem., 78, 5444, 10.1021/jo400572h

Ai, 2014, Chem. – Eur. J., 20, 17653, 10.1002/chem.201405077

Jeong, 2014, Org. Lett., 16, 4598, 10.1021/ol502173d

Zhang, 2014, J. Org. Chem., 79, 6490, 10.1021/jo500902n

Lam, 2014, Org. Biomol. Chem., 12, 4112, 10.1039/C4OB00512K

Sun, 2015, Adv. Synth. Catal., 357, 2469, 10.1002/adsc.201500125

Yu, 2015, J. Am. Chem. Soc., 137, 1623, 10.1021/ja511796h

Qiu, 2015, Org. Lett., 17, 1810, 10.1021/acs.orglett.5b00674

Cheng, 2015, Angew. Chem., Int. Ed., 54, 12349, 10.1002/anie.201501583

Shi, 2015, Chem. Commun., 51, 668, 10.1039/C4CC08407A

Zhou, 2015, Angew. Chem., Int. Ed., 54, 12121, 10.1002/anie.201505302

J. A. Joule and K.Mills, Heterocycl. Chem., Blackwell Science Ltd, Oxford, 2000

T. Eicher and S.Hauptmann, The Chemistry of Heterocycles, Wiley-VCH, Weinheim, 2003

R. J. Sundberg , Indoles, Academic Press, London, 1996

Chen, 2005, Chem. Rev., 105, 4671, 10.1021/cr050521a

Humphrey, 2006, Chem. Rev., 106, 2875, 10.1021/cr0505270

Fischer, 1983, Ber. Dtsch. Chem. Ges., 16, 2241, 10.1002/cber.188301602141

Hughes, 1993, Org. Prep. Proced. Int., 25, 607, 10.1080/00304949309356257

Larock, 1991, J. Am. Chem. Soc., 113, 6689, 10.1021/ja00017a059

Guo, 2015, Tetrahedron Lett., 56, 296, 10.1016/j.tetlet.2014.11.114

Mishra, 2014, Chem. Commun., 50, 2350, 10.1039/C3CC49486A

Sharma, 2014, Org. Biomol. Chem., 12, 1703, 10.1039/C3OB42605J

Han, 2014, Org. Lett., 16, 2494, 10.1021/ol500865j

Park, 2015, J. Org. Chem., 80, 1818, 10.1021/jo502733q

Han, 2015, J. Org. Chem., 80, 8026, 10.1021/acs.joc.5b01149

Cui, 2008, J. Am. Chem. Soc., 130, 13526, 10.1021/ja805706r

Gong, 2013, J. Am. Chem. Soc., 135, 10630, 10.1021/ja405742y

Chaitanya, 2013, Org. Lett., 15, 4960, 10.1021/ol402201c

Mishra, 2015, Adv. Synth. Catal., 357, 1293, 10.1002/adsc.201401152

Hesp, 2011, J. Am. Chem. Soc., 133, 11430, 10.1021/ja203495c

Muralirajan, 2012, Org. Lett., 14, 4262, 10.1021/ol302000a

Jeong, 2015, J. Org. Chem., 80, 7243, 10.1021/acs.joc.5b00763

Jana, 2009, Chem. – Eur. J., 15, 9078, 10.1002/chem.200901331

Tiwari, 2015, Org. Lett., 17, 1766, 10.1021/acs.orglett.5b00535

Simmons, 2012, Angew. Chem., Int. Ed., 51, 3066, 10.1002/anie.201107334