The Renaissance of Organo Nitriles in Organic Synthesis.
C−H bond functionalization
alkyne insertion
annulations
carbocycles
cycloadditions
heterocycles
nucleophilic or radical cascades
Journal
Chemistry, an Asian journal
ISSN: 1861-471X
Titre abrégé: Chem Asian J
Pays: Germany
ID NLM: 101294643
Informations de publication
Date de publication:
02 Nov 2022
02 Nov 2022
Historique:
revised:
31
08
2022
received:
02
08
2022
pubmed:
2
9
2022
medline:
2
9
2022
entrez:
1
9
2022
Statut:
ppublish
Résumé
In the arena of functional group-oriented organic synthesis, nitrile or cyano functionality is of immense importance. The presence of nucleophilic N-atom, π-coordinating ability of the triple bond, and electrophilic C-center imparts unique and interesting reactivities. Owing to the ability of the nitrile to transform into various other functional groups or intermediates, the chemistry is very rich and diverse. In particular, the involvement of nitrile in numerous organic reactions such as inter- or intramolecular alkyne insertion, [2+2+2] cycloaddition with alkynes, [3+2] cycloaddition with azides, [4+2] cycloaddition with dienes allow the synthesis of many important carbo- and heterocycles. Furthermore, the nitrile serves as a directing group in many C-H bond functionalization reactions to introduce diverse functionalities and participate as a radical acceptor in radical cascade strategies to obtain a large variety of functional molecules. This review mainly focuses on the reactivity and diverse synthetic application of the nitrile including C-H bond functionalization, alkyne insertion, cycloaddition, and thermal or photochemical cascade strategy. The objective of the current review aims at bringing out the striking collection of various nitrile-triggered organic transformations.
Identifiants
pubmed: 36047749
doi: 10.1002/asia.202200792
doi:
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202200792Subventions
Organisme : CSIR 02
ID : 0361/EMR-II
Organisme : Department of Science and Technology (DST/SERB)
ID : EMR/2016/007042
Organisme : Department of Science and Technology (DST/SERB)
ID : MHRD: 5-5/2014-TS-VII (SB/S1/OC-53/2013)
Informations de copyright
© 2022 Wiley-VCH GmbH.
Références
R. J. Billedeau, K. R. Klein, D. Kaplan, Y. Lou, Org. Lett. 2013, 15, 1421-1423;
B. L. Pagenkopf, N. Vemula, Eur. J. Org. Chem. 2017, 2561-2567;
J. A. Garduῆo, J. J. García, ACS Catal. 2020, 10, 8012-8022;
J.-C. Hsieh, H.-L. Su, Synthesis 2020, 52, 819-833;
S.-Q. Cui, W.-W. Liao, Synthesis 2022, 54, 33-48.
B. Zhao, X. Lu, Org. Lett. 2006, 8, 5987-5990;
X. Xin, D. Xiang, J. Yang, Q. Zhang, F. Zhou, D. Dong, J. Org. Chem. 2013, 78, 11956-11961;
S. Werkmeister, C. Bornschein, K. Junge, M. Beller, Eur. J. Org. Chem. 2013, 3671-3674;
D. B. Bagala, B. M. Bhanage, Adv. Synth. Catal. 2015, 357, 883-900;
M.-X. Wang, Acc. Chem. Res. 2015, 48, 602-611;
K. Cheng, M. Meng, C. Qi, Org. Chem. Front. 2017, 4, 398-403;
B. Paul, M. Maji, S. Kundu, ACS Catal. 2019, 9, 10469-10476.
K. Sun, Q.-Y. Lv, Y.-W. Lin, B. Yu, W.-M. He, Org. Chem. Front. 2021, 8, 445-465.
L. Ackermann, Chem. Rev. 2011, 111, 1315-1345;
D. A. Colby, A. S. Tsai, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2012, 45, 814-825;
K. M. Engle, T.-S. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res. 2012, 45, 788-802;
G. Rouquet, N. Chatani, Angew. Chem. Int. Ed. 2013, 52, 11726-11743;
Angew. Chem. 2013, 125, 11942-11959;
Z. Chen, B. Wang, J. Zhang, W. Yu, Z. Liu, Y. Zhang, Org. Chem. Front. 2015, 2, 1107-1295;
J. R. Hummel, J. A. Boerth, J. A. Ellman, Chem. Rev. 2017, 117, 9163-9227;
K.-X. Tang, C.-M. Wang, T.-H. Gao, L. Chen, L. Fan, L.-P. Sun, Adv. Synth. Catal. 2019, 361, 26-38.
Y. Ping, L. Wang, Q. Ding, Y. Peng, Adv. Synth. Catal. 2017, 359, 3274-3291.
W. Li, Z. Xu, P. Sun, X. Jiang, M. Fang, Org. Lett. 2011, 13, 1286-1290.
L. Wan, N. Dastbaravardeh, G. Li, J.-Q. Yu, J. Am. Chem. Soc. 2013, 135, 18056-18059.
S. Maiti, Y. Li, S. Sasmal, S. Guin, T. Bhattacharya, G. K. Lahiri, R. S. Paton, D. Maiti, Nat. Commun. 2022, 13, 3963-3972.
B. Du, X. Jiang, P. Sun, J. Org. Chem. 2013, 78, 2786-2791.
M. C. Reddy, M. Jeganmohan, Chem. Commun. 2015, 51, 10738-10741.
D. Leow, G. Li, T. S. Mei, J.-Q. Yu, Nature. 2012, 486, 518-522;
Y.-F. Yang, G.-J. Cheng, P. Liu, D. Leow, T.-Y. Sun, P. Chen, X. Zhang, J.-Q. Yu, Y.-D. Wu, K. N. Houk, J. Am. Chem. Soc. 2013, 136, 344-355.
A. Modak, A. Mondal, R. Watile, S. Mukherjee, D. Maiti, Chem. Commun. 2016, 52, 13916-13919;
M. Bera, S. Agasti, R. Chowdhury, R. Mondal, D. Pal, D. Maiti, Angew. Chem. Int. Ed. 2017, 56, 5272-5276;
Angew. Chem. 2017, 129, 5356-5360.
J. Bang, S. Gi, Y. Lee, K. L. Tan, S. Lee, Org. Lett. 2022, 24, 5181-5185.
M. Bera, A. Modak, T. Patra, A. Maji, D. Maiti, Org. Lett. 2014, 16, 5760-5763;
M. Bera, A. Maji, S. K. Sahoo, D. Maiti, Angew. Chem. Int. Ed. 2015, 54, 8515-8519;
Angew. Chem. 2015, 127, 8635-8639;
T. Patra, R. Watile, S. Agasti, T. Naveen, D. Maiti, Chem. Commun. 2016, 52, 2027-2030;
M. Bera, S. K. Sahoo, D. Maiti, ACS Catal. 2016, 6, 3575-3579.
S. Bag, P. Tatra, A. Modak, A. Deb, S. Maity, U. Dutta, A. Dey, R. Kancherla, M. Aaji, A. Hazra, M. Bera, D. Maiti, J. Am. Chem. Soc. 2015, 137, 11888-11891.
T. Patra, S. Bag, R. Kancherla, A. Mondal, A. Dey, S. Pimparkar, S. Agasti, A. Modak, D. Maiti, Angew. Chem. Int. Ed. 2016, 55, 7751-7755;
Angew. Chem. 2016, 128, 7882-7886.
U, Dutta, S. Maiti, S. Pimparkar, S. Maiti, L. R. Gahan, E. H. Krenske, D. W. Lupton, D. Maiti, Chem. Sci. 2019, 10, 7426-7432.
S. Sasmal, G. Prakash, U. Dutta, R. Laskar, G. K. Lahiri, D. Maiti, Chem. Sci. 2022, 13, 5616-5621.
W. Li, P. Sun, J. Org. Chem. 2012, 77, 8362-8366.
R. Y. Tang, G. Li, J.-Q. Yu, Nature. 2014, 507, 215-220.
A. Maji, B. Bhaskararao, S. Singha, R. B. Sunoj, D. Maiti, Chem. Sci. 2016, 7, 3147-3153.
S. Pimparkar, T. Bhattacharya, A. Maji, A. Saha, R. Jayarajan, U. Dutta, G. Lu, D. W. Lupton, D. Maiti, Chem. Eur. J. 2020, 26, 11558-11564.
L. Ackermann, Acc. Chem. Res. 2014, 47, 281-295;
Y. Yang, K. Li, Y. Cheng, D. Wan, M. Li, J. You, Chem. Commun. 2016, 52, 2872-2884;
G. Duarah, P. P. Kaishap, T. Begum, S. Gogoi, Adv. Synth. Catal. 2019, 361, 654-672;
B. K. Patel, A. Rakshit, IntechOpen. 2021, 10.5772/intechopen.95987.
F. F. Fleming, Q. Wang, Chem. Rev. 2003, 103, 2035-2077;
S. F. Rach, F. E. Kühn, Chem. Rev. 2009, 109, 2061-2080.
A. A. Pletnev, Q. Tian, R. C. Larock, J. Org. Chem. 2002, 67, 9276-9287.
Q. Tian, A. A. Pletnev, R. C. Larock, J. Org. Chem. 2003, 68, 339-347.
T. Miura, M. Murakami, Org. Lett. 2005, 7, 3339-3341.
H. Tsukamoto, T. Ikeda, T. Doi, J. Org. Chem. 2016, 81, 1733-1745.
A. Rakshit, H. N. Dhara, A. K. Sahoo, T. Alam, B. K. Patel, Org. Lett. 2022, 24, 3741-3746.
T. Takahashi, F.-Y. Tsai, Y. Li, H. Wang, Y. Kondo, M. Yamanaka, K. Nakajima, M. Kotora, J. Am. Chem. Soc. 2002, 124, 5059-5067;
J. A. Varela, C. Saa, Chem. Rev. 2003, 103, 3787-3801;
P. R. Chopade, J. Louie, Adv. Synth. Catal. 2006, 348, 2307-2327;
B. Heller, M. Hapke, Chem. Soc. Rev. 2007, 36, 1085-1094;
G. Domínguez, J. Pérez-Castells, Chem. Soc. Rev. 2011, 40, 3430-3444.
M. M. McCormick, H. A. Duong, G. Zuo, J. Louie, J. Am. Chem. Soc. 2005, 127, 5030-5031;
R. M. Stolley, H. A. Duong, J. Louie, Organometallics 2013, 32, 4952-4960.
G. Onodera, Y. Shimizu, J. Kimura, J. Kobayashi, Y. Ebihara, K. Kondo, K. Sakata, R. Takeuchi, J. Am. Chem. Soc. 2012, 134, 10515-10531.
X. You, X. Xie, G. Wang, M. Xiong, R. Sun, H. Chen, Y. Liu, Chem. Eur. J. 2016, 22, 16765-16769.
Y. Xie, C. Wu, C. Jia, C.-H. Tung, W. Wang, Org. Chem. Front. 2020, 7, 2196-2201.
C.-S. Wang, Q. Sun, F. García, C. Wang, N. Yoshikai, Angew. Chem. Int. Ed. 2021, 60, 9627-9634.
S. Huvelle, P. Matton, C. Tran, M.-N. Rager, M. Haddad, V. Ratovelomanana-Vidal, Org. Lett. 2022, 24, 5126-5131.
G. Song, D. Chen, C.-L. Pan, R. H. Crabtree, X. Li, J. Org. Chem. 2010, 75, 7487-7490;
L. Ackermann, A. V. Lygin, N. Hofmann, Org. Lett. 2011, 13, 3278-3281;
L. Ackermann, A. V. Lygin, N. Hofmann, Angew. Chem. Int. Ed. 2011, 50, 6379-6382;
Angew. Chem. 2011, 123, 6503-6506;
L. Ackermann, S. Fenner, Org. Lett. 2011, 13, 6548-6551;
H. Zhong, D. Yang, S. Wang, J. Huang, Chem. Commun. 2012, 48, 3236-3238;
L. Grigorjeva, O. Daugulis, Angew. Chem. Int. Ed. 2014, 53, 10209-10212;
Angew. Chem. 2014, 126, 10373-10376;
Z.-Q. Wang, C. Hou, Y.-F. Zhong, Y.-X. Lu, Z.-Y. Mo, Y.-M. Pan, H.-T. Tang, Org. Lett. 2019, 21, 9841-9845.
M. C. Reddy, R. Manikandan, M. Jeganmohan, Chem. Commun. 2013, 49, 6060-6062.
A. Rakshit, P. Sau, S. Ghosh, B. K. Patel, Adv. Synth. Catal. 2019, 361, 3824-3836.
P. K. Mishra, S. Chatterjee, A. K. Verma, ACS Omega. 2020, 5, 32133-32139.
J. Li, L. Chen, E. Chin, A. S. Lui, H. Zecic, Tetrahedron Lett. 2010, 51, 6422-6425.
H. Shen, Z. Xie, J. Am. Chem. Soc. 2010, 132, 11473-11480.
R. Kumar, M. Asthana, R. M. Singh, J. Org. Chem. 2017, 82, 11531-11542.
X. Liu, G. Deng, Y. Liang, Tetrahedron Lett. 2018, 59, 2844-2847.
F. Himo, Z. P. Demko, L. Noodleman, K. B. Sharpless, J. Am. Chem. Soc. 2002, 124, 12210-12216.
D. P. Matthews, J. E. Green, A. J. Shuker, J. Comb. Chem. 2000, 2, 19-23;
G. Venkateshwarlu, A. Premalatha, K. C. Rajanna, P. K. Saiprakash, Synth. Commun. 2009, 39, 4479-4485;
G. Venkateshwarlu, K. C. Rajanna, P. K. Saiprakash, Synth. Commun. 2009, 39, 426-432;
M. Nasrollahzadeh, Y. Bayat, D. Habibi, S. Moshaee, Tetrahedron Lett. 2009, 50, 4435-4438;
B. Sreedhar, A. S. Kumar, D. Yada, Tetrahedron Lett. 2011, 52, 3565-3569;
S. M. Agawane, J. M. Nagarkar, Catal. Sci. Technol. 2012, 2, 1324-1327;
R. Shelkar, A. Singh, J. Nagarkar, Tetrahedron Lett. 2013, 54, 106-109.
Z. P. Demko, K. B. Sharpless, J. Org. Chem. 2001, 66, 7945-7950.
Z. P. Demko, K. B. Sharpless, Angew. Chem. 2002, 114, 2217-2220;
Angew. Chem. Int. Ed. 2002, 41, 2113-2116.
D. Amantini, R. Beleggia, F. Fringuelli, F. Pizzo, L. Vaccaro, J. Org. Chem. 2004, 69, 2896-2898.
M. L. Kantam, K. B. S. Kumar, C. Sridhar, Adv. Synth. Catal. 2005, 347, 1212-1214.
L. Bosch, J. Vilarrasa, Angew. Chem. Int. Ed. 2007, 46, 3926-3930;
Angew. Chem. 2007, 119, 4000-4004.
T. Jin, F. Kitahara, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 2008, 49, 2824-2827.
J. Bonnamour, C. Bolm, Chem. Eur. J. 2009, 15, 4543-4545.
B. Das, C. R. Reddy, D. N. Kumar, M. Krishnaiah, R. Narender, Synlett 2010, 3, 391-394.
L. Lang, B. Li, W. Liu, L. Jiang, Z. Xu, G. Yin, Chem. Commun. 2010, 46, 448-450.
V. Rama, K. Kanagaraj, K. Pitchumani, J. Org. Chem. 2011, 76, 9090-9095.
S. Kumar, S. Dubey, N. Saxena, S. K. Awasthi, Tetrahedron Lett. 2014, 55, 6034-6038.
P. Mani, A. K. Singh, S. K. Awasthi, Tetrahedron Lett. 2014, 55, 1879-1882.
M. Ohashi, I. Takeda, M. Ikawa, S. Ogoshi, J. Am. Chem. Soc. 2011, 133, 18018-18021.
T. Watanabe, S. Ueda, S. Inuki, S. Oishi, N. Fujii, H. Ohno, Chem. Commun. 2007, 4516-4518;
P.-Y. Yao, Y. Zhang, R. P. Hsung, K. Zhao, Org. Lett. 2008, 10, 4275-4278;
J. Zhu, H. Xie, Z. Chen, S. Li, Y. Wu, Chem. Commun. 2009, 2338-2340;
A. K. Verma, T. Kesharwani, J. Singh, V. Tandon, R. C. Larock, Angew. Chem. Int. Ed. 2009, 48, 1138-1143;
Angew. Chem. 2009, 121, 1158-1163;
X. Lv, W. J. Bao, J. Org. Chem. 2009, 74, 5618-5621;
F. Wang, S. Cai, Q. Liao, C. Xi, J. Org. Chem. 2011, 76, 3174-3180;
L.-L. Zhang, S. Chen, Y.-Z. Gao, P.-B. Zhang, Y.-L. Wu, G. Tang, Y.-F. Zhao, Org. Lett. 2016, 18, 1286-1289;
P.-B. Zhang, L.-L. Zhang, Y.-Z. Gao, G. Tang, Y.-F. Zhao, RSC Adv. 2016, 6, 60922-60925;
S.-S. Wang, H. Fu, G. Wang, M. Sunb, Y.-M. Li, RSC Adv. 2016, 6, 52391-52394;
W. Chen, Y. Zhang, P. Li, L. Wang, Org. Chem. Front. 2018, 5, 855-859.
A. A. Pletnev, R. C. Larock, J. Org. Chem. 2002, 67, 9428-9438;
C. Zhou, R. C. Larock, J. Org. Chem. 2006, 71, 3551-3558.
H. N. Dhara, A. Rakshit, T. Alam, B. K. Patel, Org. Biomol. Chem. 2022, 20, 4243-4277.
S. Ueda, H. Nagasawa, J. Am. Chem. Soc. 2009, 131, 15080-15081.
Y.-F. Chen, J.-C. Hsieh, Org. Lett. 2014, 16, 4642-4645.
C. Li, S. An, Y. Zhu, J. Zhang, Y. Kang, P. Liu, Y. Wang, J. Li, RSC Adv. 2014, 4, 49888-49891.
X. Yu, L. Gao, L. Jia, Y. Yamamoto, M. Bao, J. Org. Chem. 2018, 83, 10352-10358.
Y. Jaiswal, Y. Kumar, J. Pal, R. Subramanian, A. Kumar, Chem. Commun. 2018, 54, 7207-7210.
T.-T. Wang, D. Zhang, W.-W. Liao, Chem. Commun. 2018, 54, 2048-2051.
J. Xie, H. Huang, T. Xu, R. Li, J. Chen, X. Ye, RSC Adv. 2020, 10, 8586-8593.
L. Dai, S. Yu, N. Lv, X. Ye, Y. Shao, Z. Chen, J. Chen, Org. Lett. 2021, 23, 5664-5668.
A. Rakshit, H. N. Dhara, T. Alam, A. Dahiya, B. K. Patel, J. Org. Chem. 2021, 86, 17504-17510.
W. Li, H. Zhou, Y. He, G. Zeng, Y. Zheng, Y. Hu, Z. Chen, J.-Y. Ge, N. Lv, J. Chen, Org. Lett. 2022, 24, 5090-5094.
J. Zheng, Y. Zhang, D. Wang, S. Cui, Org. Lett. 2016, 18, 1768-1771.
J.-Q. Shang, S.-S. Wang, H. Fu, Y. Li, T. Yang, Y.-M. Li, Org. Chem. Front. 2018, 5, 1945-1949.
L.-J. Wu, Y. Yang, R.-J. Song, J.-X. Yu, J.-H. Li, D.-L. He, Chem. Commun. 2018, 54, 1367-1370.
X.-H. Shan, H.-X. Zheng, B. Yang, L. Tie, J.-L. Fu, J.-P. Qu, Y.-B. Kang, Nat. Commun. 2019, 10, 908-916.
P. Xu, Y.-M. Zhu, F. Wang, S.-Y. Wang, S.-J. Ji, Org. Lett. 2019, 21, 683-686.
J.-Q. Shang, X.-X. Wang, Y. Xin, Y. Li, B. Zhou, Y.-M. Li, Org. Biomol. Chem. 2019, 17, 9447-9455.
J. Guo, Y. Hao, G. Li, Z. Wang, Y. Liu, Y. Li, Q. Wang, Org. Biomol. Chem. 2020, 18, 1994-2001.
W. Fu, F. Xu, Y. Fu, M. Zhu, J. Yu, C. Xu, D. Zou, J. Org. Chem. 2013, 78, 12202-12206;
S. Tang, Y.-L. Deng, J. Li, W.-X. Wang, G.-L. Ding, M.-W. Wang, Z.-P. Xiao, Y.-C. Wang, R.-L. Sheng, J. Org. Chem. 2015, 80, 12599-12605;
G. Bergonzini, C. Cassani, C.-J. Wallentin, Angew. Chem. Int. Ed. 2015, 54, 14066-14069;
Angew. Chem. 2015, 127, 14272-14275;
L. Zhou, M. L. Hossain, T. Xiao, Chem. Rec. 2016, 16, 319-334;
W. Ji, H. Tan, M. Wang, P. Li, L. Wang, Chem. Commun. 2016, 52, 1462-1465;
D. Xia, Y. Li, T. Miao, P. Li, L. Wang, Green Chem. 2017, 19, 1732-1739;
Q. Deng, Y. Xu, P. Liu, L. Tan, P. Sun, Org. Chem. Front. 2018, 5, 19-23.
X. Sun, J. Li, Y. Ni, D. Ren, Z. Hu, S. Yu, Asian J. Org. Chem. 2014, 3, 1317-1325.
Y.-Y. Han, H. Jiang, R. Wang, S. Yu, J. Org. Chem. 2016, 81, 7276-7281.
X. Li, X. Fang, S. Zhuang, P. Liu, P. Sun, Org. Lett. 2017, 19, 3580-3583.
Y. Yu, Z. Cai, W. Yuan, P. Liu, P. Sun, J. Org. Chem. 2017, 82, 8148-8156.
Y. Yu, W. Yuan, H. Huang, Z. Cai, P. Liu, P. Sun, J. Org. Chem. 2018, 83, 1654-1660.
P. Natarajan, M. Muskan, N. K. Brar, J. J. Kaur, Org. Chem. Front. 2018, 5, 1527-1531.
X. Liu, Z. Wu, Z. Zhang, P. Liu, P. Sun, Org. Biomol. Chem. 2018, 16, 414-423.
M. Zhu, W. Fu, W. Guo, Y. Tian, Z. Wang, B. Ji, Org. Biomol. Chem. 2019, 17, 3374-3380.
A. K. Sahoo, A. Rakshit, A. Dahiya, A. Pan, B. K. Patel, Org. Lett. 2022, 24, 1918-1923.