- A General C(sp3)-C(sp3) Cross-Coupling of Benzyl Sulfonylhydrazones with Alkyl Boronic Acids
-
A general transition-metal-free cross-coupling between benzylic sulfonylhydrazones and 1°, 2°, or 3° alkyl boronic acids is reported. The base-promoted reaction is operationally simple and exhibits a broad substrate scope to forge a variety of alkyl-alkyl bonds, including between sterically encumbered secondary and tertiary sp3-carbons. The ability of this method to simplify retrosynthetic analysis is exemplified by the improved synthesis of multiple medicinally relevant scaffolds.
- Merchant, Rohan R.,Lopez, Jovan A.
-
supporting information
p. 2271 - 2275
(2020/03/13)
-
- Coupling of Trifluoroacetaldehyde N-Triftosylhydrazone with Organoboronic Acids for the Synthesis of gem-Difluoroalkenes
-
The synthesis of alkyl gem-difluoroalkenes remains a difficult task in organic synthesis. Here, we report a general and efficient approach for tackling this problem by gem-difluoroolefination of trifluoroacetaldehyde N-triftosylhydrazone with organoboronic acids. This protocol is operationally simple, free of transition metals, and suitable for a broad range of organoboronic acids. Moreover, the utility of the products was demonstrated by further conversion of the gem-difluorovinyl group.
- Ma, Yu,Reddy, Bhoomireddy Rajendra Prasad,Bi, Xihe
-
p. 9860 - 9863
(2019/12/24)
-
- Visible-Light-Mediated Aerobic Oxidation of Organoboron Compounds Using in Situ Generated Hydrogen Peroxide
-
A simple and general visible-light-mediated oxidation of organoboron compounds has been developed with rose bengal as the photocatalyst, substoichiometric Et3N as the electron donor, as well as air as the oxidant. This mild and metal-free protocol shows a broad substrate scope and provides a wide range of aliphatic alcohols and phenols in moderate to excellent yields. Notably, the robustness of this method is demonstrated on the stereospecific aerobic oxidation of organoboron compounds.
- Weng, Wei-Zhi,Liang, Hao,Zhang, Bo
-
supporting information
p. 4979 - 4983
(2018/08/24)
-
- Palladium-catalyzed borylation of primary alkyl bromides
-
A mild Pd-catalyzed process for the borylation of alkyl bromides has been developed using bis(pinacolato)diboron as a boron source. This process accommodates the use of a wide range of functional groups on the alkyl bromide substrate. Primary bromides react with complete selectivity in the presence of a secondary bromide. The generality of this approach is demonstrated by its extension to the use of alkyl iodides and alkyl tosylates, as well as borylation reactions employing bis(neopentyl glycolato)diboron as the boron source.
- Joshi-Pangu, Amruta,Ma, Xinghua,Diane, Mohamed,Iqbal, Sidra,Kribs, Robert J.,Huang, Richard,Wang, Chao-Yuan,Biscoe, Mark R.
-
scheme or table
p. 6629 - 6633
(2012/09/22)
-
- Copper-promoted trifluoromethylation of primary and secondary alkylboronic acids
-
New couple: The Cu-promoted trifluoromethylation of primary and secondary alkylboronic acids with TMSCF3 extends the scope of transition-metal-catalyzed trifluoromethylation reactions to sp 3-hybridized carbon centers. It also repres
- Xu, Jun,Xiao, Bin,Xie, Chuan-Qi,Luo, Dong-Fen,Liu, Lei,Fu, Yao
-
supporting information
p. 12551 - 12554
(2013/02/22)
-
- Iron trichloride promoted hydrolysis of potassium organotrifluoroborates
-
In the presence of iron trichloride, the hydrolysis of potassium organotrifluoroborates occurs smoothly at room temperature to afford the corresponding organoboronic acids in good to excellent yields. The hydrolysis is effective for aryltrifluoroborates as well as alkenyl- and alkyl- trifluoroborates.
- Blevins, David W.,Yao, Min-Liang,Yong, Li,Kabalka, George W.
-
experimental part
p. 6534 - 6536
(2011/12/22)
-
- P1 Phenethyl peptide boronic acid inhibitors of HCV NS3 protease
-
A series of peptide boronic acids containing extended, hydrophobic P1 residues was prepared to probe the shallow, hydrophobic S1 region of HCV NS3 protease. The p-trifluoromethylphenethyl P1 substituent was identified as optimal with respect to inhibitor potency for NS3 and selectivity against elastase and chymotrypsin.
- Priestley,De Lucca, Indawati,Ghavimi, Bahman,Erickson-Viitanen, Susan,Decicco, Carl P.
-
p. 3199 - 3202
(2007/10/03)
-
- Synthesis of η-arene derivatives of chromium and molybdenum containing Lewis-acid boron substituents
-
The compounds Ph(CH2)3B(OH)2 I, [Ph(CH2)3BO]3 II, Ph(CH2)3B(1,2-O2C6H4) III, Ph(CH2)3BC8H14 IV (BC8H14 = 9-borabicyclo[3.3.1]nonan-9-yl), [Cr{η-Ph(CH2)3B(1,2-O2C6H 4)}(CO)3] 1, [Cr{η-Ph(CH2)3BC8H14}(CO) 3] 2, [Cr{η-Ph(CH2)3BBr2·SMe 2}(CO)3] 3, [Cr{η-Ph(CH2)4BC8H14}(CO) 3] 4, [Cr(η-Ph(CH2)4BC8H14}(CO) 2(PPh3)] 5, [Cr{η-PhCH2CH=CH2}(CO)3] 6, [Cr{η-Ph(CH2)2CH=CH2}(CO)3] 7, [Cr{η-Ph(CH2)2η-CH=CH2}(CO) 2] 8, [Cr{η-Ph(CH2)2CH=CH2}(CO) 2(PPh3)] 9, [Li(Et2O)n][Cr{η-PhCH2CH=CH 2}(CO)2{C(O)Ph}] 10, [Li(Et2O)n][Cr{η-Ph(CH2) 2CH=CH2}(CO)2{C(O)Ph}] 11, [Mo{η-Ph(CH2)3BC8H14} 2] 12 and [Cr{η-Ph(CH2)3BOC8H14}(CO) 3] 13, have been prepared and characterised. Compounds 1-5, 12 and 13 have π-donor η-arene ligands which also bear a Lewis-acid α-acceptor boron group. There was no evidence that these boron groups formed ground-state intra- or inter-molecular interactions with the Lewis base functions of the carbonyl oxygen atoms.
- Green, Malcolm L. H.,Wagner, Matthias
-
p. 2467 - 2473
(2007/10/03)
-