Seminar

Seminar

B–H Functionalization of o-Carborane

  • POSTED DATE : 2022-09-08
  • WRITER : 화학과
  • HIT : 254
  • DATE : 2022년 9월 8일(목) 오후 4시 30분
  • PLACE : 330226호실

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제  목 : B–H Functionalization of o-Carborane

연  사 : 이필호 교수(강원대학교)
일  시 : 2022년 9월 8일(목오후 4시 30분

장  소 : 화학관 2층 330226

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B–H Functionalization of o-Carborane


Phil Ho Lee

Center for Catalytic Organic Reactions & Department of Chemistry

Kangwon National University, Chuncheon, Korea

E-mail: phlee@kangwon.ac.kr


Carboranes, which are recognized as a type of three-dimensional kindred of benzene, have found a number of applications in boron neutron capture therapy (BNCT) as medication, in organometallic and coordination chemistry as novel ligands, and in supramolecular design and materials as building blocks. However, the distinctive structures of carboranes make their derivatization laborious, which results in a restricted application range. Therefore, it is highly required to develop new synthetic methods for the functionalization of carboranes. In general, cage boron functionalization is much more challenging than cage carbon functionalization because of not only its site-selectivity among ten cage B−H bonds over only three reactive sites in arene C−H activation but also its much lower reactivity of cage B−H over cage C−H bond. Herein, we present transition metal-catalyzed cyclative indenylation, dienylation, allenylation, amidation, acyloxyation, diacetoxylation, acylmethylation, pyrazolization, and triarylation of o-carboranes.

R1CO2HR1HArR3R1ZR4R3R5HNR2OHHHHNOR2HR1HHNR2OR1HOAcOAcR1HOR2OHHNMeO2CR1OR2Na= C,other == BBHcatR1HNHAr3Ar2Ar1R2OR1CO2H (CO2Me, H)R2OR1HR2OR1HR2OR1R3OR1HR2OR2ON2NNOR2H

References

1. Baek, Y.; Cheong, K.; Ko, G. H.; Han, G. U.; Han, S. H.; Kim, D.; Lee, K.; Lee, P. H.* J. Am. Chem. Soc. 2020, 142, 9890.

2. Baek, Y.; Kim, S.; Son, J.-Y.; Lee, K.; Kim, D.; Lee, P. H.* ACS Catal. 2019, 9, 10418.

3. Ko, G. H.; Um, K.; Noh, H. C.; Kim, J. Y.; Jeong, H.; Maeng, C.; Han, S. H.; Han, G. U.; Lee, P. H.* Org. Lett. 2022, 24, 1604.

4. Shin, S.; Um, K.; Ko, G. H.; Han, G. U.; Kim, D.; Lee, P. H.* Org. Lett. 2022, 24, 3128.

5. Maeng, C.; Ko, G. H.; Yang, H.; Han, S. H.; Han, G. U.; Noh, H. C.; Lee, K.; Kim, D.; Lee, P. H.* Org. Lett. 2022, 24, 3526.

6. Han, G. U.; Baek, Y.; Lee, K.; Shin, S.; Noh, H. C.; Lee, P. H.* Org. Lett. 2021, 23, 416.

7. Baek, Y.; Cheong, K.; Kim, D.; Lee, P. H.* Org. Lett. 2021, 23, 1188.

8. Han, G. U.; Shin, S.; Baek, Y.; Kim, D.; Lee, K.; Kim, J. G.; Lee, P. H.* Org. Lett. 2021, 23, 8622.

9. Ham, H.; Shin, S.; Ko, G. H.; Han, S. H.; Han, G. U.; Maeng, C.; Kim, T. H.; Noh, H. C.; Lee, K.; Kim, H.; Yang, H.; Lee, P. H.* J. Org. Chem. 2021, 86, 15153.

10. Ko, G. H.; Lee, J. K.; Han, S.; Lee, P. H.* Org. Lett. 2022, 24, 1507.