Chemo-, Regio-, and Stereoselective cis-Hydroboration of 1,3-Enynes: Copper-Catalyzed Access to (Z,Z)- and (Z,E)-2-Boryl-1,3-dienes

被引：3

作者：

Buchbinder, Nicklas W. ^{[1
]}

Nguyen, Long H. ^{[1
]}

Beck, Owen N. ^{[1
]}

Bage, Andrew D. ^{[1
]}

Slebodnick, Carla ^{[1
]}

Santos, Webster L. ^{[1
]}

机构：

[1] Virginia Tech, Dept Chem, Blacksburg, VA 24061 USA

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 29期

基金：

美国国家科学基金会;

关键词：

ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC HYDROBORATION; BORON; FLUORESCENCE; ENYNES; DIYNES;

D O I：

10.1021/acs.orglett.4c01929

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed alkyne-selective hydroboration of 1,3-enynes is disclosed, providing access to the previously elusive 2-boryl-1,3-dienes. Using CuOAc, Xantphos, and HBpin, Bpin was installed on the internal carbon of a series of symmetric and nonsymmetric 1,3-enynes, affording products with excellent Z:E selectivity. The utility of the 2-boryl-1,3-diene products was demonstrated by transformation to useful functional groups.

引用

页码：6136 / 6141

页数：6

共 33 条

[1] Suzuki-Miyaura cross-couplings for alkyl boron reagent: recent developments-a review [J].

Ahmed, Adnan ;

Mushtaq, Irfan ;

Chinnam, Sampath .

FUTURE JOURNAL OF PHARMACEUTICAL SCIENCES, 2023, 9 (01)

[2] Hidden Boron Catalysis: Nucleophile-Promoted Decomposition of HBpin [J].

Bage, Andrew D. ;

Hunt, Thomas A. ;

Thomas, Stephen P. .

ORGANIC LETTERS, 2020, 22 (11) :4107-4112

[3] First-Row d-Block Element-Catalyzed Carbon-Boron Bond Formation and Related Processes [J].

Bose, Shubhankar Kumar ;

Mao, Lujia ;

Kuehn, Laura ;

Radius, Udo ;

Nekvinda, Jan ;

Santos, Webster L. ;

Westcott, Stephen A. ;

Steel, Patrick G. ;

Marder, Todd B. .

CHEMICAL REVIEWS, 2021, 121 (21) :13238-13341

[4] Regio- and Stereoselective Copper-Catalyzed Borylation-Protodeboronation of 1,3-Diynes: Access to (Z)-1,3-Enynes [J].

Burgio, Ariel L. ;

Buchbinder, Nicklas W. ;

Santos, Webster L. .

ORGANIC LETTERS, 2023, 25 (15) :2652-2656

[5]

ccdc, About us

[6] Boron Chemicals in Drug Discovery and Development: Synthesis and Medicinal Perspective [J].

Das, Bhaskar C. ;

Nandwana, Nitesh K. ;

Das, Sasmita ;

Nandwana, Varsha ;

Shareef, Mohammed Adil ;

Das, Yogarupa ;

Saito, Mariko ;

Weiss, Louis M. ;

Almaguel, Frankis ;

Hosmane, Narayan S. ;

Evans, Todd .

MOLECULES, 2022, 27 (09)

[7] Recent advances in Chan-Lam coupling reaction [J].

Devi, P. S. ;

Saranya, Salim ;

Anilkumar, Gopinathan .

CATALYSIS SCIENCE & TECHNOLOGY, 2024, 14 (09) :2320-2351

[8] Highly sensitive fluorescence probes for nitric oxide based on boron dipyrromethene chromophore-rational design of potentially useful bioimaging fluorescence probe [J].

Gabe, Y ;

Urano, Y ;

Kikuchi, K ;

Kojima, H ;

Nagano, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (10) :3357-3367

[9] Catalytic, Enantioselective Synthesis of Allenyl Boronates [J].

Gao, De-Wei ;

Xiao, Yiyang ;

Liu, Mingyu ;

Liu, Zhen ;

Karunananda, Malkanthi K. ;

Chen, Jason S. ;

Engle, Keary M. .

ACS CATALYSIS, 2018, 8 (04) :3650-3654

[10] The transition metal-catalysed hydroboration reaction [J].

Geier, Stephen J. ;

Vogels, Christopher M. ;

Melanson, Jennifer A. ;

Westcott, Stephen A. .

CHEMICAL SOCIETY REVIEWS, 2022, 51 (21) :8877-8922

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