Progress in the Transition Metal-Catalyzed Addition Reaction of OrganoboronicAcids to Unsaturated Bonds

Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (5): 472-484. Previous Articles Next Articles

过渡金属催化的有机硼酸与不饱和键的加成反应

焦宁^a, 叶龙武^b, 麻生明^*,a,b

^a中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032
^b浙江大学化学系杭州 310027

收稿日期:2003-05-22 修回日期:2003-09-05 接受日期:2003-10-09 发布日期:2022-09-20

Progress in the Transition Metal-Catalyzed Addition Reaction of OrganoboronicAcids to Unsaturated Bonds

JIAO, Ning^a, YE, Long-Wu^b, MA, Sheng-Ming^*,a,b

^aState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
^bDepartment of Chemistry, Zhejiang University, Hangzhou 310027

Received:2003-05-22 Revised:2003-09-05 Accepted:2003-10-09 Published:2022-09-20
Contact: *E-mail: masm@mail.sioc.ac.cn

Abstract

Organoboronic acids enjoy high prestige in the metal-catalyzed C—Cbond formation. The cross-coupling reaction of organoboron compound has been proved to be a quite general technique for a wide range of selective C—C bondformation. In the past few years, much attention has been paid to the transition metal-catalyzed addition of organoboronic acids to unsaturated C—C bond, aldehydes and N-sulfonyl imines. The most notable progress is the developmentof the asymmetric addition affording the corresponding optically active 1,4-addition product effectively. In this paper, we will summarize the most recent progress in the Rh-, Ni- and Pd-catalyzed 1,4- or 1,2-additions of organoboronicacids.

Key words: metal-catalyzed, addition reaction, organoboronic acid, asymmetric, arylation

Cite this article

JIAO, Ning, YE, Long-Wu, MA, Sheng-Ming. Progress in the Transition Metal-Catalyzed Addition Reaction of OrganoboronicAcids to Unsaturated Bonds[J]. Chinese Journal of Organic Chemistry, 2004, 24(5): 472-484.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

1 Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics1997, 16, 4229.
2 Dekker, G. P. C.; Elsevier, C. J.; Vrieze, K. Organometallics 1992, 11, 1588.
3 Takaya, Y.; Ogasawara, M.; Havashi, T.; Sakai, M.; Miyaura, N.J. Am. Chem. Soc. 1998, 120, 5579.
4 Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052.
5 (a) Lane, C. F.; Kabalka, G. W. Tetrahedron 1976, 32, 981.
(b) Brown, H. C.; Gupta, S. K. J. Am. Chem. Soc. 1975, 97, 5249.
6 Takaya, Y.; Ogasawara, M.; Havashi, T. Tetrahedron Lett. 1998, 39, 8479.
7 Takaya, Y.; Ogasawara, M.; Hayashi, T. Chirality 2000, 12, 469.
8 Hayashi, T. Synlett 2001, 879.
9 (a) Kuriyama, M.; Tomioka, K. Tetrahedron Lett. 2001, 42, 921.
(b) Kuriyama, M.; Nagai, K.; Yamada, K.; Miwa, Y.; Taga, T.; Tomioka, K.J. Am. Chem. Soc. 2002, 124, 8932.
10 (a) Boiteau, J.-G.; Imbos, R.; Minnaard, A. J.; Feringa, B. L. Org.Lett. 2003, 5, 681.
(b) Reetz, M. T.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083.
11 Itooka, R.; Iguchi, Y.; Miyaura, N. J. Org. Chem. 2003,68, 6000.
12 (a) Takaya, Y.; Ogasawara, M. Tetrahedron Lett. 1999, 40, 6957.
(b) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Havashi, T. Tetrahedron: Asymmetry 1999, 10, 4047.
(c) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951.
13 Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464.
14 Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martin-Matute, B. J.Am. Chem. Soc. 2001, 123, 5358.
15 Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918.
16 For a review on the nickel-catalyzed addition: Houpis, I. N.; Lee, J.Tetrahedron 2000, 56, 817.
17 For a review on the organozinc reagents: Knochel, P.; Almena Perea, J.J.; Jones, P. Tetrahedron 1998, 54, 8275.
18 For a review on the cross-coupling of organoboron reagents: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
19 (a) For a review on the organotitanium reagents: Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835.
(b) Gao, Y.; Harada, K.; Hata, T.; Urabe, H.; Sato, F. J. Org. Chem.1995, 60, 290.
20 For reviews:
(a) Tamura, R.; Kamimrea, A.; Ono, N. Synthesis 1991, 423.
(b) Fuji, K.; Node, M. Synlett 1991, 603.
21 Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H.E. J. Am. Chem. Soc. 1999, 121, 10215.
22 Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716.
23 Takaya, Y.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 1998, 120, 5579.
24 Hayashi, T.; Senda, T.; Takaya, Y.;Ogasawara, M. J. Am. Chem. Soc.1999, 11591.
25 (a) Yamamoto, H. Lewis Acids in Organic Synthesis, Wiley-VCH, Weinheim, 2000.
(b) Chapman, C. J.; Frost, C. G.; Harttey, J. P.; Whittle, A. J. Tetrahedron Lett. 2001, 42, 773.
26 Frost, C. G.; Wadsworth, K. J. Chem. Commun. 2001, 2316.
27 (a) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem. 1998, 110, 3475; Angew. Chem., Int. Ed. 1998, 37,3279.
(b) Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65,4450.
28 (a) Angermund, K.; Baumann, W.; Dinjus, E.; Fornika, R.; Gürls, H.; Kessler, M.; Krüger, K.; Leitner, W.; Lutz, F. Chem. Eur. J. 1997, 3, 755.
(b) Casey, C. P.; Whiteker, G. T.; Melville, M. G.; Petrovich, L. M.; GavneyJr., J. A.; Powell, D. R. J. Am. Chem. Soc. 1992, 114, 5535.
(c) Kranenburg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; Van Leeuwen,P. W. N. M.; Goubitz, K.; Fraanje, J. Organometallics 1995. 14, 3081.
(d) Fornika, R.; Görls, H.; Seemann, B.; Leitner, W. J. Chem. Soc., Chem. Commun. 1995, 1479.
29 Fürstner, A.; Krause, H. Adv. Synth. Catal. 2001, 343, 343.
30 Ishiyama, T.; Ahiko, T.-A.; Miyaura, N. J. Am. Chem. Soc. 2002, 124, 12414.
31 Ueda, M.; Miyaura, N. J. Organomet. Chem. 2000, 595, 31.
32 Ueda, M.; Saito, A.; Miyaura, N. Synlett 2000, 1637.
33 Shirakawa, E.; Yoshida H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221.
34 Shirakawa, E.; Nakao, Y.; Yoshida H.; Hiyama, T. J. Am. Chem. Soc. 2000, 122, 9030.
35 Shirakawa, E.; Nakao Y.; Hiyama, T. Chem. Commun. 2001,263.
36 Shirakawa, E.; Yamamoto, Y.; Nakao, Y.; Tsuchimoto T.; Hiyama, T. Chem. Commun. 2001, 1926.
37 Shirakawa, E.; Takahashi, G.; Tsuchimoto, T.; Kawakami, Y. Chem. Commun. 2001, 2688.
38 Shirakawa, E.; Takahashi, G.; Tsuchimoto, T.; Kawakami, Y. Chem. Commun. 2002, 2210.
39 (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
(b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
40 (a) Hayashi, T.; Niizuma, S.; Kamikawa, T.; Suzuki, N.; Uozumi, Y. J.Am. Chem. Soc. 1995, 117, 9101.
(b) Kamikawa, T.; Hayashi, T. Tetrahedron 1999, 55, 3455.
41 (a) Burk, M. J.; Allen, J. G.; Kiesman, W. F. J. Am. Chem. Soc. 1998, 120, 657.
(b) Hénaff, N.; Whiting, A. J. Chem. Soc., Perkin Trans. 12000, 395.
42 (a) Roush, W. R.; Moriarty, K. J.; Brown, B. B. Tetrahedron Lett.1990, 31, 6509.
(b) Uenishi, J.; Kawahama, R.; Yonemitsu, O.; Tsuji, J. J. Org. Chem. 1996, 61, 5716.
43 Oh, C. H.; Jung, H. H.; Kim, K. S.; Kim, N. Angew. Chem., Int. Ed.2003, 42, 805.

[1]	Shuang Yang, Xinqiang Fang. Kinetic Resolutions Enabled by N-Heterocyclic Carbene Catalysis: An Update [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 448-480.
[2]	Wanting Chen, Xiongwei Zhong, Jiale Xing, Changshu Wu, Yang Gao. Progress in Asymmetric Catalytic Synthesis of C—N Axis Chiral Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 349-377.
[3]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[4]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[5]	Quanbin Jiang. Progress in Synthesis of Axially Chiral Compounds through aza-Vinylidene o-Quinone Methide Intermediates [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 159-172.
[6]	Hao Qin, Chuanjin Hou, Dinghua Liang, Xinwei He, Ling Li, Xiangping Hu. Chiral P,N,N-Ligands for Pd-Catalyzed Asymmetric Allylic Substitutions [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 282-290.
[7]	Xiao Song, Jing Qing, Jun Li, Xuelei Jia, Fusong Wu, Junrong Huang, Jian Jin, Hengzhi You. Copper-Catalyzed Asymmetric Allyl Alkylation Using Grignard Reagents under Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3174-3179.
[8]	Wenfang Wang. Recent Progress in Transition-Metal-Catalyzed Asymmetric C—H Borylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3146-3166.
[9]	Junjie Zhang, Xuetao Xu. [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3297-3303.
[10]	Chun-Xia Cheng, Lu-Ping Wu, Feng Sha, Xin-Yan Wu. Enantioselective Vinylogous Allylic Alkylation of Coumarins with Morita-Baylis-Hillman Carbonates Catalyzed by Chiral Phosphine-Amide [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3188-3195.
[11]	Zujia Chen, Shiwei Yu, Yongjun Zhou, Huanqing Li, Qiwen Qiu, Miaoxin Li, Zhaoyang Wang. Application of BF₃•OEt₂ in Organic Synthesis as a Catalyst or Synthon [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3107-3118.
[12]	Zuliang Chen, Yingjing Wei, Junliang Zhang. Recent Advances in Cycloaddition Reactions of Donor-Acceptor Aziridines via Carbon-Carbon Bond Cleavage [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3078-3088.
[13]	Yi Wang, Jian Zhang, Yangzi Liu, Xiaoyan Luo, Weiping Deng. Palladium-Catalyzed Asymmetric [3＋4] Cycloadditions for the Construction of Cyclohepta[b]indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2864-2877.
[14]	Zhangtao Zhou, Yang Wang, Bingxin Cheng, Weiping Ye. [RuCl(p-cymene)-(S)-BINAP]Cl Catalyzed Asymmetric Preparation of trans-3-Amino-bicyclo[2.2.2]octane-2-carboxylic Acid Ethyl Ester [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2961-2967.
[15]	Yuchao Wang, Jinbiao Liu, Zhitao He. Palladium-Catalyzed Asymmetric Hydrofunctionalizations of Conjugated Dienes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2614-2627.

过渡金属催化的有机硼酸与不饱和键的加成反应

Progress in the Transition Metal-Catalyzed Addition Reaction of OrganoboronicAcids to Unsaturated Bonds

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments