78782-17-9 (二(4,4,5,5-四甲基-1,3,2-二氧杂戊硼烷-2-基)甲烷,Bis[(pinacolato)boryl]methane)

_84%

反应条件：

1.1 Reagents: Lithium methoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ; 24 h, 40 °C

参考文献：

Copper-Catalyzed/Promoted Cross-coupling of gem-Diborylalkanes with Nonactivated Primary Alkyl Halides: An Alternative Route to Alkylboronic Esters

Zhang, Zhen-Qi; Yang, Chu-Ting; Liang, Lu-Jun; Xiao, Bin; Lu, Xi; et al, Organic Letters, 2014, 16(24), 6342-6345

合成路线：1 步

70557-99-2

_90%

364634-18-4

反应条件：

1.1 Reagents: Sodium Solvents: Benzene

参考文献：

Addition Reactions of Bis(pinacolato)diborane(4) to Carbonyl Enones and Synthesis of (pinacolato)2BCH2B and (pinacolato)2BCH2CH2B by Insertion and Coupling

Ali, Hijazi Abu; Goldberg, Israel; Srebnik, Morris, Organometallics, 2001, 20(18), 3962-3965

合成路线：1 步

_83%

反应条件：

1.1 Reagents: Tetrabutylammonium iodide , Potassium methoxide Catalysts: Copper Solvents: Dimethylformamide ; 24 h, 80 °C

参考文献：

Facile synthesis of alkyl- and arylboronate esters enabled by a carbon nanotube supported copper catalyst

Saini, Suresh; Gavali, Deepak S.; Bhawar, Ramesh; Thapa, Ranjit; Dhayal, Rajendra S.; et al, Catalysis Science & Technology, 2023, 13(1), 147-156

合成路线：1 步

_81%

反应条件：

1.1 Catalysts: Cupric chloride , 1,3-Bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene Solvents: Tetrahydrofuran ; 10 min, rt
1.2 Reagents: Potassium methoxide ; 10 min, rt
1.3 1 h, 60 °C

参考文献：

Highly efficient synthesis of alkylboronate esters via Cu(II)-catalyzed borylation of unactivated alkyl bromides and chlorides in air

Bose, Shubhankar Kumar; Brand, Simon; Omoregie, Helen Oluwatola; Haehnel, Martin; Maier, Jonathan; et al, ACS Catalysis, 2016, 6(12), 8332-8335

合成路线：1 步

_80%

反应条件：

1.1 Reagents: Lithium methoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ; 24 h, 40 °C

参考文献：

Direct Light-Enabled Access to α-Boryl Radicals: Application in the Stereodivergent Synthesis of Allyl Boronic Esters

Marotta, Alessandro; Fang, Hao; Adams, Callum E.; Sun Marcus, Kailey; Daniliuc, Constantin G.; et al, Angewandte Chemie, 2023, 62(34),

合成路线：1 步

_80%

反应条件：

1.1 Reagents: Lithium methoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ; 24 h, 40 °C

参考文献：

Direct light-enabled access to α-boryl radicals: application in the stereodivergent synthesis of allyl boronic esters

Marotta, Alessandro; Fang, Hao; Adams, Callum E.; Marcus, Kailey Sun; Daniliuc, Constantin G.; et al, ChemRxiv, 2023, 1, 1-9

合成路线：1 步

75-11-6

_80%

反应条件：

1.1 Reagents: Chloro(1-methylethyl)magnesium Solvents: Tetrahydrofuran ; 20 min, -78 °C; 2.5 h, -78 °C
1.2 30 min, -78 °C; -78 °C → -55 °C; 24 h, -55 °C
1.3 Reagents: Ammonium chloride Solvents: Water ; -55 °C; -55 °C → rt

参考文献：

Enantio- and Diastereoselective Synthesis of 1,2-Hydroxyboronates through Cu-Catalyzed Additions of Alkylboronates to Aldehydes

Joannou, Matthew V.; Moyer, Brandon S.; Meek, Simon J., Journal of the American Chemical Society, 2015, 137(19), 6176-6179

合成路线：1 步

_79%

反应条件：

1.1 Reagents: Lithium methoxide Catalysts: Triphenylphosphine , Cuprous iodide Solvents: Dimethylformamide ; 24 h, rt

参考文献：

A Catalytic Enantiotopic-Group-Selective Suzuki Reaction for the Construction of Chiral Organoboronates

Sun, Chunrui; Potter, Bowman; Morken, James P., Journal of the American Chemical Society, 2014, 136(18), 6534-6537

合成路线：1 步

_78%

反应条件：

1.1 Reagents: Lithium methoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ; 10 min, rt
1.2 12 h, rt

参考文献：

A Boron Alkylidene-Alkene Cycloaddition Reaction: Application to the Synthesis of Aphanamal

Liu, Xun; Deaton, T. Maxwell; Haeffner, Fredrik; Morken, James P., Angewandte Chemie, 2017, 56(38), 11485-11489

合成路线：1 步

_78%

反应条件：

1.1 Reagents: Lithium methoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ; 10 min, rt
1.2 12 h, rt

参考文献：

Simple access to elusive α-boryl carbanions and their alkylation: an umpolung construction for organic synthesis

Hong, Kai; Liu, Xun; Morken, James P., Journal of the American Chemical Society, 2014, 136(30), 10581-10584

合成路线：1 步

_77%

反应条件：

1.1 Catalysts: Cupric chloride , 1,3-Bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene Solvents: Tetrahydrofuran ; 10 min, rt
1.2 Reagents: Potassium methoxide ; 10 min, rt; 60 °C

参考文献：

A site-selective and stereospecific cascade Suzuki-Miyaura annulation of alkyl 1,2-bisboronic esters and 2,2'-dihalo 1,1'-biaryls

Willems, Suzanne; Toupalas, Georgios; Reisenbauer, Julia C.; Morandi, Bill, Chemical Communications (Cambridge, 2021, 57(32), 3909-3912

合成路线：1 步

_75%

反应条件：

1.1 Reagents: Lithium methoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ; rt; 24 h, rt

参考文献：

Enantiomerically Enriched Tris(boronates): Readily Accessible Conjunctive Reagents for Asymmetric Synthesis

Coombs, John R.; Zhang, Liang; Morken, James P., Journal of the American Chemical Society, 2014, 136(46), 16140-16143

合成路线：1 步

76-09-5

_71%

反应条件：

1.1 Reagents: 2,2′-Bi-1,3,2-benzodioxaborole Solvents: Dimethylformamide ; 6 h, 50 °C
1.2 Reagents: Triethylamine ; 1 h, rt

参考文献：

Electrooxidative Activation of B-B Bond in B2cat2: Access to gem-Diborylalkanes via Paired Electrolysis

Wang, Bingbing; Zhang, Xiangyu; Cao, Yangmin; Zou, Long; Qi, Xiaotian ; et al, Angewandte Chemie, 2023, 62(14),

合成路线：1 步

_71%

反应条件：

1.1 Reagents: Lithium methoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ; rt

参考文献：

Synthesis of a Biomimetic Tetracyclic Precursor of Aspochalasins and Formal Synthesis of Trichoderone A

Gayraud, Oscar; Laroche, Benjamin; Casaretto, Nicolas; Nay, Bastien, Organic Letters, 2021, 23(15), 5755-5760

合成路线：1 步

_70%

反应条件：

1.1 Reagents: Tetrabutylammonium iodide , Potassium tert-butoxide Catalysts: Dopamine (anchored on ferrite) , Copper (nano-Fe-DOPA supported) Solvents: Dimethylformamide ; 24 h, 80 °C

参考文献：

Efficient synthesis of alkylboronic esters via magnetically recoverable copper nanoparticle-catalyzed borylation of alkyl chlorides and bromides

Shegavi, Mahadev L.; Agarwal, Abhishek; Bose, Shubhankar Kumar, Green Chemistry, 2020, 22(9), 2799-2803

合成路线：1 步

_70%

反应条件：

1.1 Reagents: Lithium tert-butoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ; 24 h, 40 °C

参考文献：

Base-promoted, deborylative secondary alkylation of N-heteroaromatic N-oxides with internal gem-bis[(pinacolato)boryl]alkanes: a facile derivatization of 2,2'-bipyridyl analogues

Hwang, Chiwon; Jo, Woohyun; Cho, Seung Hwan, Chemical Communications (Cambridge, 2017, 53(54), 7573-7576

合成路线：1 步

_70%

反应条件：

1.1 Reagents: Lithium tert-butoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ; 24 h, 40 °C

参考文献：

Chemoselective Coupling of 1,1-Bis[(pinacolato)boryl]alkanes for the Transition-Metal-Free Borylation of Aryl and Vinyl Halides: A Combined Experimental and Theoretical Investigation

Lee, Yeosan; Baek, Seung-yeol; Park, Jinyoung; Kim, Seoung-Tae ; Tussupbayev, Samat ; et al, Journal of the American Chemical Society, 2017, 139(2), 976-984

合成路线：1 步

_67%

反应条件：

1.1 Reagents: Lithium methoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ; 24 h, 40 °C
1.2 Solvents: Ethyl acetate

参考文献：

Organophotocatalytic N-O Bond Cleavage of Weinreb Amides: Mechanism-Guided Evolution of a PET to ConPET Platform

Soika, Julia; McLaughlin, Calum; Nevesely, Tomas; Daniliuc, Constantin G.; Molloy, John. J.; et al, ACS Catalysis, 2022, 12(16), 10047-10056

合成路线：1 步

_67%

反应条件：

1.1 Reagents: Lithium methoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ; 24 h, 40 °C
1.2 Reagents: Ethyl acetate

参考文献：

Organophotocatalytic N-O bond cleavage of Weinreb amides: mechanism-guided evolution of a PET to ConPET platform

Soika, Julia; McLaughlin, Calum; Nevesely, Tomas; Daniliuc, Constantin; Molloy, John. J.; et al, ChemRxiv, 2022, 1, 1-15

合成路线：1 步

_64%