Rhodium catalyzed cascade cyclization featuring B–H and C–H activation: one-step construction of carborane-fused N-polyheterocycles DOI Creative Commons
Hairong Lyu, Yangjian Quan, Zuowei Xie

et al.

Chemical Science, Journal Year: 2018, Volume and Issue: 9(30), P. 6390 - 6394

Published: Jan. 1, 2018

A novel Rh-catalyzed cascade cyclization featuring both carboranyl B–H and aryl C–H activation has been developed, resulting in the one-pot construction of three new B–C C–C bonds. The isolation structural identification a key intermediate provide solid evidence for reaction mechanism.

Language: Английский

Pd‐Catalyzed Selective Bifunctionalization of 3‐Iodo‐o‐Carborane by Pd Migration DOI

Yixiu Ge,

Jie Zhang, Zaozao Qiu

et al.

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 59(12), P. 4851 - 4855

Published: Dec. 25, 2019

Abstract A palladium‐catalyzed highly selective 3,4‐bifunctionalization of 3‐I‐ o ‐carborane has been developed, leading to the preparation 3‐alkenyl‐4‐R‐ ‐carboranes (R=alkyl, alkynyl, aryl, allyl, CN, and amido) in high excellent yields. This protocol combines sequential activation cage B(3)−I B(4)−H bonds by Pd migration from exo ‐alkenyl sp 2 C B(4), which is driven thermodynamic force. represents a brand‐new strategy for bifunctionalization carboranes with two different substituents.

Language: Английский

Citations

58
Regioselective B(3,4)–H arylation of o-carboranes by weak amide coordination at room temperature DOI Creative Commons
Yu‐Feng Liang, Long Yang,

Becky Bongsuiru Jei

et al.

Chemical Science, Journal Year: 2020, Volume and Issue: 11(39), P. 10764 - 10769

Published: Jan. 1, 2020

B–H: site-selective B(3,4)–H arylations were accomplished at room temperature by versatile palladium catalysis enabled weakly coordinating amides.

Language: Английский

Citations

55
Functional Group Directed B–H Activation of Polyhedral Boron Hydrides by Transition Metal Complexes (Review) DOI
Igor B. Sivaev

Russian Journal of Inorganic Chemistry, Journal Year: 2021, Volume and Issue: 66(9), P. 1289 - 1342

Published: Sept. 1, 2021

Language: Английский

Citations

53
Transient Directing Groups in Metal−Organic Cooperative Catalysis DOI
Clément Jacob, Bert U. W. Maes, Gwilherm Evano

et al.

Chemistry - A European Journal, Journal Year: 2021, Volume and Issue: 27(56), P. 13899 - 13952

Published: July 19, 2021

The direct functionalization of C-H bonds is among the most fundamental chemical transformations in organic synthesis. However, when innate reactivity substrate cannot be utilized for a given single bond, this selective bond mostly relies on use directing groups that allow bringing catalyst close proximity to activated and these need installed before cleaved after transformation, which involves two additional undesired synthetic operations. These steps dramatically reduce overall impact attractiveness techniques since classical approaches based pre-functionalization are sometimes still more straightforward appealing. During past decade, different approach involving both situ installation removal group, can then often used catalytic manner, has emerged: transient group strategy. In addition its innovative character, strategy brought an unprecedented level usefulness enabled development remarkably efficient processes introduction functional onto aromatic aliphatic substrates. unlocked by will comprehensively overviewed review article.

Language: Английский

Citations

44
Copper catalyzed/mediated direct B–H alkenylation/alkynylation in carboranes DOI
Yu Chen, Yik Ki Au, Yangjian Quan

et al.

Science China Chemistry, Journal Year: 2018, Volume and Issue: 62(1), P. 74 - 79

Published: Dec. 6, 2018

Language: Английский

Citations

58
Palladium catalyzed selective arylation of o-carboranes via B(4)–H activation: amide induced regioselectivity reversal DOI

Tao‐Tao Xu,

Ke Cao, Caiyan Zhang

et al.

Chemical Communications, Journal Year: 2018, Volume and Issue: 54(96), P. 13603 - 13606

Published: Jan. 1, 2018

By changing the charge distribution of boron vertices via introducing an amide on cage B(9), selective B(4) arylation o-carboranes Suzuki-Miyaura coupling has been developed. A series o-carborane derivatives decorated with diverse active groups have synthesized moderate to good yields, which proved be further transformed a novel kind tri-substituted nido-carborane fused oxazole potential application in neutron capture therapy, organometallic as well coordination chemistry.

Language: Английский

Citations

54
Highly selective palladium-catalyzed one-pot, five-fold B–H/C–H cross coupling of monocarboranes with alkenes DOI Creative Commons
Yunjun Shen, Kang Zhang, Xuewei Liang

et al.

Chemical Science, Journal Year: 2019, Volume and Issue: 10(15), P. 4177 - 4184

Published: Jan. 1, 2019

Palladium-catalyzed dehydrogenative B-H/C-H cross coupling of monocarborane anions with alkenes is reported, allowing for the first time isolation selectively penta-alkenylated boron clusters. The reaction cascade regioselective cage positions, leading directly to B2-6 functionalization. Under mild and convenient conditions, styrenes, benzylic aliphatic are demonstrated be viable partners exclusive vinyl-type B-C bond formation. Multiple subsequent transformations provide access directing group-free products, chiral derivatives penta-alkylated cages. five-fold coupling, combined latter reactions, represents a powerful methodology straightforward synthesis new classes

Language: Английский

Citations

46
Catalytic Oxidative Dehydrogenative Coupling of Cage B–H/B–H Bonds for Synthesis of Bis(o-carborane)s DOI

Ji Wu,

Ke Cao, Caiyan Zhang

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(15), P. 5986 - 5989

Published: July 22, 2019

An efficient and succinct protocol for synthesis of bis(o-carborane) connected by a B–B bond via palladium catalyzed oxidative dehydrogenative coupling cage B–H/B–H bonds was developed the first time. A series bis(o-carborane)s B(4)–B(4)′ B(4)–B(5)′ synthesized with moderate to good yields. This work opens door miscellaneous applications in related disciplines has important value design different kinds biscarboranes.

Language: Английский

Citations

43
One‐Pot Process to Carborano‐Coumarin via Catalytic CascadeDehydrogenative Cross‐Coupling DOI
Yik Ki Au, Hairong Lyu, Yangjian Quan

et al.

Chinese Journal of Chemistry, Journal Year: 2020, Volume and Issue: 38(4), P. 383 - 388

Published: Jan. 16, 2020

Summary of main observation and conclusion Ir‐catalyzed cascade dehydrogenative CH/BH BH/OH cross‐coupling carboranyl carboxylic acid with readily available benzoic has been achieved, leading to the facile synthesis previously unavailable carborano‐coumarin in a simple one‐pot process. Two cage B—H, one aryl C—H O—H bonds are activated construct efficiently new B—C B—O bonds. The cyclization can stop at first B—H/C—H step by tuning reaction conditions, resulting series α‐carboranyl carborane derivatives. Control experiments indicate that dehydrocoupling proceeds preferentially over B—H/O—H dehydrocoupling, both directing groups oxidants crucial for this reaction. An iridium(V) intermediate is proposed be involved catalytic cycle.

Language: Английский

Citations

40
Metal-catalyzed B–H acylmethylation of pyridylcarboranes: access to carborane-fused indoliziniums and quinoliziniums DOI Creative Commons
Hou‐Ji Cao, Xing Wei,

Fangxiang Sun

et al.

Chemical Science, Journal Year: 2021, Volume and Issue: 12(47), P. 15563 - 15571

Published: Jan. 1, 2021

Metal-catalyzed selective mono-acylmethylation of pyridylcarboranes has been realized, which provides further utility to construct carborane-fused indoliziniums and quinoliziniums.

Language: Английский

Citations

35