Divergent upgrading pathways of sulfones with primary alcohols: nickel-catalyzed α-alkylation under N2 and metal-free promoted β-olefination in open air

被引:6
作者
Yu, Haiping [1 ]
Fu, Kaiyue [1 ]
Yang, Guang [1 ]
Liu, Mengyu [1 ]
Yang, Peng [1 ,2 ]
Liu, Tao [1 ]
机构
[1] Shandong Normal Univ, Coll Chem, Chem Engn & Mat Sci, Jinan 250014, Peoples R China
[2] Taiyuan Univ Technol, State Key Lab Clean & Efficient Coal Utilizat, Taiyuan 030024, Peoples R China
基金
中国国家自然科学基金;
关键词
BORROWING HYDROGEN; UNACTIVATED AMIDES; C-ALKYLATION; KETONES; ESTERS; NITRILES; ACTIVATION; CHEMISTRY; SECONDARY; PHENYL;
D O I
10.1039/d2cc05882k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report here our findings on the diverse reaction results of sulfones and alcohols. In the presence of NiCl2/P(t-Bu)(3) and under a N-2 atmosphere, alpha-C-alkylation of sulfones with alcohols occurs through a borrowing-hydrogen mechanism; when the reaction was carried out in the open air without nickel, the product was not the predicted alpha,beta-unsaturated sulfone, but the beta-alkenyl sulfone, which is a useful building block in organic synthesis.
引用
收藏
页码:615 / 618
页数:4
相关论文
共 49 条
  • [1] Hydrogen Borrowing Catalysis with Secondary Alcohols: A New Route for the Generation of β-Branched Carbonyl Compounds
    Akhtar, Wasim M.
    Cheong, Choon Boon
    Frost, James R.
    Christensen, Kirsten E.
    Stevenson, Neil G.
    Donohoe, Timothy J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (07) : 2577 - 2580
  • [2] A DIRECT SYNTHESIS OF OLEFINS BY REACTION OF CARBONYL-COMPOUNDS WITH LITHIO DERIVATIVES OF 2-[ALKYL-SULFONYL OR (2'-ALKENYL)-SULFONYL OR BENZYL-SULFONYL]-BENZOTHIAZOLES
    BAUDIN, JB
    HAREAU, G
    JULIA, SA
    RUEL, O
    [J]. TETRAHEDRON LETTERS, 1991, 32 (09) : 1175 - 1178
  • [3] Nickel-catalyzed hydrogen-borrowing strategy: chemo-selective alkylation of nitriles with alcohols
    Bera, Sourajit
    Bera, Atanu
    Banerjee, Debasis
    [J]. CHEMICAL COMMUNICATIONS, 2020, 56 (50) : 6850 - 6853
  • [4] The modified Julia olefination:: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds
    Blakemore, PR
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (23): : 2563 - 2585
  • [5] Novel Aerobic Oxidation of Primary Sulfones to Carboxylic Acids
    Bonaparte, Amy C.
    Betush, Matthew P.
    Panseri, Bettina M.
    Mastarone, Daniel J.
    Murphy, Ryan K.
    Murphree, S. Shaun
    [J]. ORGANIC LETTERS, 2011, 13 (06) : 1447 - 1449
  • [6] Manganese-Catalyzed α-Alkylation of Ketones, Esters, and Amides Using Alcohols
    Chakraborty, Subrata
    Daw, Prosenjit
    Ben David, Yehoshoa
    Milstein, David
    [J]. ACS CATALYSIS, 2018, 8 (11): : 10300 - 10305
  • [7] Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis
    Corma, Avelino
    Navas, Javier
    Sabater, Maria J.
    [J]. CHEMICAL REVIEWS, 2018, 118 (04) : 1410 - 1459
  • [8] General and Mild Cobalt-Catalyzed C-Alkylation of Unactivated Amides and Esters with Alcohols
    Deibl, Nicklas
    Kempe, Rhett
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (34) : 10786 - 10789
  • [9] Sulfones in heterocyclic synthesis: advances in the chemistry of phenyl sulfonylacetophenone
    Elattar, Khaled M.
    Fekri, Ahmed
    Bayoumy, Nesma M.
    Fadda, Ahmed A.
    [J]. RESEARCH ON CHEMICAL INTERMEDIATES, 2017, 43 (07) : 4227 - 4264
  • [10] Strategic Application and Transformation of ortho-Disubstituted Phenyl and Cyclopropyl Ketones To Expand the Scope of Hydrogen Borrowing Catalysis
    Frost, James R.
    Cheong, Choon Boon
    Akhtar, Wasim M.
    Caputo, Dimitri F. J.
    Stevenson, Neil G.
    Donohoe, Timothy J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (50) : 15664 - 15667