En Route to Direct Cross-Coupling between Carbonyl Derivatives and Allyl Alcohols via Hydrazones

被引:1
作者
Gui, Ruohua [1 ,2 ]
Alaghemand, Faraz [1 ,2 ]
Khaliullin, Rustam Z. [1 ,2 ]
Li, Chao-Jun [1 ,2 ]
机构
[1] McGill Univ, Dept Chem, Montreal, PQ H3A 0B8, Canada
[2] McGill Univ, FQRNT Ctr Green Chem & Catalysis, Montreal, PQ H3A 0B8, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
allylation; nickel catalysis; hydrazones; HOME chemistry; green chemistry; SOFT NUCLEOPHILES; ALPHA-ALLYLATION; BIOMASS; SUBSTITUTION; ALDEHYDES; ALKYLATION; ACTIVATION; CATALYSIS; DEPROTECTION; ADDITIONS;
D O I
10.1021/acscatal.4c07971
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Allylic cross-couplings are pivotal in the organic chemistry toolbox; however, traditional methods require the extensive use of noble metals and are limited to activated substrates. To date, allylic cross-couplings that utilize affordable metals and unactivated allylic alcohols remain unexplored. Herein, we report a distinct coupling of ubiquitous and commercially available aldehydes with unactivated allyl alcohols, which also benefits from generating only water and nitrogen gas as innocuous byproducts. This operationally simple and mild methodology enables the direct allylation of carbonyl derivatives, affording alkene products in moderate to high yields across 40 substrates. The reported conditions tolerate both aryl and alkyl aldehydes, as well as ketones with a variety of functional groups. Notably, our strategy facilitates the expedited synthesis of value-added chemicals while producing environmentally benign byproducts.
引用
收藏
页码:5943 / 5953
页数:11
相关论文
共 66 条
[11]   Umpolung Addition of Aldehydes to Aryl Imines [J].
Chen, Ning ;
Dai, Xi-Jie ;
Wang, Haining ;
Li, Chao-Jun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (22) :6260-6263
[12]   K3PO4-Catalyzed Regiospecific Aminobromination of β-Nitrostyrene Derivatives with N-Bromoacetamide as Aminobrominating Agent [J].
Chen, Zhan-Guo ;
Wang, Yun ;
Wei, Jun-Fa ;
Zhao, Peng-Fei ;
Shi, Xian-Ying .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (06) :2085-2088
[13]  
Colacot J., 2008, Ferrocenes, P117
[14]   A concise update on the applications of chiral ferrocenyl phosphines in homogeneous catalysis leading to organic synthesis [J].
Colacot, TJ .
CHEMICAL REVIEWS, 2003, 103 (08) :3101-3118
[15]   Carbonyls as Latent Alkyl Carbanions for Conjugate Additions [J].
Dai, Xi-Jie ;
Wang, Haining ;
Li, Chao-Jun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (22) :6302-6306
[16]   SELECTIVE CLEAVAGE OF THE ALLYL AND ALLYLOXCARBONYL GROUPS THROUGH PALLADIUM-CATALYZED HYDROSTANNOLYSIS WITH TRIBUTYLTIN HYDRIDE - APPLICATION TO THE SELECTIVE PROTECTION-DEPROTECTION OF AMINO-ACID DERIVATIVES AND IN PEPTIDE-SYNTHESIS [J].
DANGLES, O ;
GUIBE, F ;
BALAVOINE, G ;
LAVIELLE, S ;
MARQUET, A .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) :4984-4993
[18]   Recent Advances in Direct Catalytic Dehydrative Substitution of Alcohols [J].
Dryzhakov, Marian ;
Richmond, Edward ;
Moran, Joseph .
SYNTHESIS-STUTTGART, 2016, 48 (07) :935-959
[19]   Direct Nucleophilic SN1-Type Reactions of Alcohols [J].
Emer, Enrico ;
Sinisi, Riccardo ;
Capdevila, Montse Guiteras ;
Petruzziello, Diego ;
De Vincentiis, Francesco ;
Cozzi, Pier Giorgio .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (04) :647-666
[20]   Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis [J].
Feng, Jiajie ;
Kasun, Zachary A. ;
Krische, Michael J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (17) :5467-5478