Application of Triborylmethane Reagent in the Stereoselective Synthesis of Dissymmetric gem-Diborylalkenes

doi:10.6023/cjoc202406008

Chinese Journal of Organic Chemistry

ARTICLE

次甲基三硼试剂在非对称烯基偕二硼立体选择性合成中的应用研究

杨甜甜^a,b, 陈都^a,b, 张鹏^*,a, 刘超^*,a

^a中国科学院兰州化学物理研究所羰基合成与选择性氧化国家重点实验室兰州 730000;
^b中国科学院大学北京 100049

收稿日期:2024-06-07 修回日期:2024-08-11

Application of Triborylmethane Reagent in the Stereoselective Synthesis of Dissymmetric gem-Diborylalkenes

Yang Tiantian^a,b, Chen Du^a,b, Zhang Peng^*,a, Liu Chao^*,a

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, CAS, Lanzhou 730000, P. R. China;
^bUniversity of Chinese Academy of Sciences, Beijing 100049, P. R. China

Received:2024-06-07 Revised:2024-08-11
Contact: *E-mail: pengzhang@licp.cas.cn; chao.liu@nju.edu.cn

1. .pdf(2444KB)

Abstract

In this work, we successfully synthesized a novel triborylmethane reagent, which reacts with aldehydes, pentamethyldiethylenetriamine (PMDETA) as an additive, enabling the synthesis of dissymmetrical gem-diborylalkenes. The method exhibits excellent stereoselectivity and good yields. The reaction has good substrate compatibility and the two boryl moieties in the product have different reactivities. Through cross-coupling with aryl halides, the Bpin moiety can be converted into an aryl group, achieving the stereoselective synthesis of trisubstituted vinylboronates.

Key words: gem-diborylalkenes, B-O elimination, Boron reagent, Aldehydes

Cite this article

Yang Tiantian, Chen Du, Zhang Peng, Liu Chao. Application of Triborylmethane Reagent in the Stereoselective Synthesis of Dissymmetric gem-Diborylalkenes[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202406008.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Miyaura, N.; Suzuki, A.Chem. Rev. 1995, 95, 2457.
(b) Lennox A. J. J.; Lloyd-Jones, G. C. Chem. Soc. Rev.2014, 43, 412.
(c) Geier S. J.; Westcott, S. A. Rev. Inorg. Chem.2015, 35, 69.
(d) Tian M.; Yang L.; Liu B.; Chang, J. Chin. J. Chem.2023, 41, 1327.
(e) Zhu D.; Zhao Y.; Chong Q.; Meng, F. Chin. J. Chem.2022, 40, 190.
(f) Zhang L.; Du Q.; Luo Y.; Wang Y.; Gao F.; Ye Y.; Zhang, W. Chin. J. Chem.2023, 41, 3003.
(j) Gao X.; Ren X.; Deng W.; Zhang, X. Chin. J. Chem.2023, 41, 3521.
[2] (a) Shimizu M.; Nakamaki C.; Shimono K.; Schelper M.; Kurahashi T.; Hiyama, T. J. Am. Chem. Soc.2005, 127, 12506.
(b) Shimizu M.; Nagao I.; Tomioka Y.; Hiyama, T. Angew. Chem. Int. Ed.2008, 47, 8096.
(c) Yavari K.; Moussa S.; BenβHassine B.; Retailleau P.; Voituriez A.; Marinetti, A. Angew. Chem. Int. Ed.2012, 51, 6748.
[3] (a) Shimizu, M.; Shimono, K.; Schelper, M.; Hiyama, T.Synlett 2007, 2007, 1969.
(b) Takaya J.; Kirai N.; Iwasawa, N. J. J. Am. Chem. Soc.2011, 133, 12980.
(c) Wen H.; Zhang L.; Zhu S.; Liu G.; Huang Z. ACS Catal.2017, 7, 6419.
(d) Procter R. J.; Uzelac M.; Cid J.; Rushworth P. J.; Ingleson, M. J. ACS Catal.2019, 9, 5760.
(e) Yoshii D.; Jin X.; Mizuno N.; Yamaguchi K. ACS Catal.2019, 9, 3011.
(f) Lee C.; Shih W.; Zhou J.; Reibenspies J. H.; Ozerov, O. V. Angew. Chem. Int. Ed.2015, 54, 14003.
[4] Morinaga A.; Nagao K.; Ohmiya H.; Sawamura, M. Angew. Chem. Int. Ed.2015, 54, 15859.
[5] Ho H. E.; Asao N.; Yamamoto Y.; Jin T. Org. Lett.2014, 16, 4670.
[6] Krautwald S.; Bezdek M. J.; Chirik, P. J. J. Am. Chem. Soc.2017, 139, 3868.
[7] Liu X.; Ming W.; Luo X.; Friedrich A.; Maier J.; Radius U.; Santos W. L.; Marder T. B.Eur. J. Org. Chem. 2020, 2020, 1941.
[8] Gao Y.; Wu Z.; Engle, K. M. Org. Lett.2020, 22, 5235.
[9] Lou X.; Lin J.; Kwok C. Y.; Lyu, H. Angew. Chem. Int. Ed.2023, 62, e202312633.
[10] Chen D.; Xu L.; Wang Z.; Liu C. Chem2023, 9, 3212.
[11] Chen D.; Xu L.; Yu Y.; Mo Q.; Qi X.; Liu, C. Angew. Chem. Int. Ed.2023, 62, e202215168.
[12] Namirembe S.; Gao C.; Wexler R. P.; Morken, J. P. Org. Lett.2019, 21, 4392.
[13] Matteson D. S.; Moody R. J. Organometallics1982, 1, 20.
[14] (a) Hu Y.; Sun W.; Zhang T.; Xu N.; Xu J.; Lan Y.; Liu, C. Angew. Chem. Int. Ed.2019, 58, 15813.
(b) Wang S.; Chen C.; Zeng, X. Chin. J. Org. Chem.2023, 43, 2447 (in Chinese).
(王莎, 陈常鹏, 曾小明, 有机化学, 2023, 43, 2447.)
(c) Reid W. B.; Watson, D. A. Org. Lett.2018, 20, 6832.
(d) Cuenca A. B.; Fernández, E. Chem. Soc. Rev.2021, 50, 72.
(e) Coombs J. R.; Zhang L.; Morken, J. P. Org. Lett.2015, 17, 1708.
(f) Kovalenko M.; Yarmoliuk D. V.; Serhiichuk D.; Chernenko D.; Smyrnov V.; Breslavskyi A.; Hryshchuk O. V.; Kleban I.; Rassukana Y.; Tymtsunik A. V.; Tolmachev A. A.; Kuchkovska Y. O.; Grygorenko, O. O. Eur. J. Org. Chem.2019, 2019, 5624.
(g) Endo K.; Hirokami M.; Shibata, T. J. Org. Chem.2010, 75, 3469.
(h) Kuang Z.; Chen H.; Yan J.; Yang K.; Lan Y.; Song Q. Org. Lett.2018, 20, 5153.
(i) La Cascia E.; Cuenca A. B.; Fernández, E. Chem. - Eur. J.2016, 22, 18737.

[1]	Longlong Li, Xinyue He, Longsheng Zhou, Hengtong Qu, Chengtao Feng, Kun Xu. NH₄SCN-Promoted Formal [3＋3] Annulation for the Synthesis of 5-Arylated Pyrazolo[1,5-a]pyrimidines [J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2832-2840.
[2]	Ming Zhao, Rui Yan, Hu Chen. N-Heterocyclic Carbene Catalyzed the Umpolung of Aldehyde Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2204-2215.
[3]	Mengjin Liu, Yan Xiao, Kai Zhou, Zicheng Li, Wencai Huang. Synthesis of 3,5-Diaryl-1,2,4-oxadiazole by One-Pot Homocoupling Reaction [J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2251-2256.
[4]	Rou Ding, Siyu Shi, Chao Ma, Wei Wei, Yufen Lü. Metal-Free 1,8-Diazabicyclo(5.4.0)-undec-7-ene Mediated Synthesis of α-Acetal Amides through Reaction of Glyoxylic Acid Acetalde with Aryl Isothiocyanates [J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2216-2222.
[5]	Yufei Zhou, Xiaofei Jia. Progress in Heterogeneous Catalyzed Tandem Reactions Based on Hydroformylation [J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 3147-3158.
[6]	Wenqian Wu, Chunxia Chen, Jinsong Peng, Zhanyu Li. Research Progress of Carbonyl α-Position Amination [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2743-2763.
[7]	Lu Liu, Shuguang Zhang, Renwei Hu, Xiaoxiao Zhao, Jingnan Cui, Weitao Gong. Synthesis and Properties of Phenolic Resin Polymers Based on Pillar[5]arene [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2808-2814.
[8]	Yiwen Quan, Xinhui Jiang, Wenjun Li, Jian Wang. Access to α-Vinyl β-Alkynyl Enals via an Organocatalytic Deconjugation-Aldol Condensation Sequence [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2120-2125.
[9]	Min Lü, Aimei Yang, Yu Zhang, Jianting Sun, Bangguo Wei. Fe(OTf)₃-Catalyzed Synthesis of Boronic Ester Containing N,O-Acetal Structure [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1777-1785.
[10]	Wenhan Yang, Jiwen Jiao, Xiaoming Wang. Merging Electron Transfer Activation with 1,2-Metalate Migration: Deoxygenative Silylation of Amides [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1857-1867.
[11]	Xuzheng Zhang, Fengli Yu, Bing Yuan, Congxia Xie, Shitao Yu. Phase Transfer Catalytic Oxidation of Cyclopentene to Glutaraldehyde by Vanadium Molybdenum Heteropolyacid Salts [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1444-1451.
[12]	Jingpeng Li, Shuntao Huang, Qi Yang, Weiqiang Li, Teng Liu, Chao Huang. A Practical Synthesis of (Z)-N-Vinyl Substituted N,O-Acetals under Continuous Flow Technology [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1550-1558.
[13]	Yuliang Chen, Fengkai He, Siyun Wang, Dingcheng Jia, Yaqun Liu, Yiyong Huang. Kinetic Resolution of Aldehydes Bearing an All-Carbon Quaternary Stereocenter at the α-Position by the Antilla Allylboration [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4294-4302.
[14]	Yongling Wang, Tiexin Zhang, Xuming Zhang, Hanyang Sun, Jinyao Leng, Yaming Li. Synthesis of Unnatural Amino Acid Derivatives by Visible- Light-Catalyzed Decarboxylative Alkylation of N-Aromatic Glyoxylimines [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4284-4293.
[15]	Fasheng Shi, Shengwen Wang, Huan Xu, Xingxing Lu, Xinling Yang, Tengda Sun, Changkai Wang, Xiaoming Zhang, Qing Yang, Yun Ling. Design, Synthesis and Fungicidal Actiνity of Noνel Thiosemicarbazide Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2106-2116.

次甲基三硼试剂在非对称烯基偕二硼立体选择性合成中的应用研究

Application of Triborylmethane Reagent in the Stereoselective Synthesis of Dissymmetric gem-Diborylalkenes

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments