Metallaphotoredox-Mediated Decarboxylative Cross-Coupling of α-Oxy Morpholine Carboxylic Acids and (Hetero)Aryl Halides

被引:7
作者
Sloane, Jack L. [1 ]
Santos, Anna Beatriz [1 ]
Simmons, Eric M. [2 ]
Sherwood, Trevor C. [3 ]
机构
[1] Bristol Myers Squibb, Small Mol Drug Discovery, Cambridge, MA 02142 USA
[2] Bristol Myers Squibb, Chem Proc Dev, New Brunswick, NJ 08903 USA
[3] Bristol Myers Squibb, Small Mol Drug Discovery, Princeton, NJ 08543 USA
关键词
EFFICIENT SYNTHESIS; PHOTOREDOX; CHEMISTRY;
D O I
10.1021/acs.orglett.3c01478
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A decarboxylative C(sp(2))-C(sp(3)) cross-couplingreaction of alpha-oxy carboxylic acids using dual nickel/photoredoxcatalysis has been developed for the synthesis of complex morpholinesand other saturated heterocycles, affording direct entry to scaffoldsof interest in drug discovery. This chemistry can be applied to thecoupling of an array of (hetero)aryl halides and alpha-heteroatomacids, providing C(sp(2))-C(sp(3))-coupledproducts in modest to excellent yields and enabling access to intermediatesthat can be further derivatized to multivector architectures.
引用
收藏
页码:4219 / 4224
页数:6
相关论文
共 43 条
  • [1] Ahneman DT, 2016, CHEM SCI, V7, P7002, DOI [10.1039/c6sc02815b, 10.1039/C6SC02815B]
  • [2] Akahoshi I., 2019, Novel Heteroaromatic Amide Derivative and Medicine Containing Same, Patent No. [WO2020054657, 2020054657]
  • [3] Carboxylic Acids as Adaptive Functional Groups in Metallaphotoredox Catalysis
    Beil, Sebastian B.
    Chen, Tiffany Q.
    Intermaggio, Nicholas E.
    MacMillan, David W. C.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2022, 55 (23) : 3481 - 3494
  • [4] Efficient synthesis of NK1 receptor antagonist aprepitant using a crystallization-induced diastereoselective transformation
    Brands, KMJ
    Payack, JF
    Rosen, JD
    Nelson, TD
    Candelario, A
    Huffman, MA
    Zhao, MM
    Li, J
    Craig, B
    Song, ZGJ
    Tschaen, DM
    Hansen, K
    Devine, PN
    Pye, PJ
    Rossen, K
    Dormer, PG
    Reamer, RA
    Welch, CJ
    Mathre, DJ
    Tsou, NN
    McNamara, JM
    Reider, PJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (08) : 2129 - 2135
  • [5] A compact, practical photoreactor for multi-reaction arrays
    Brown, Gregory D.
    Batalla, Daniel
    Cavallaro, Cullen L.
    Perez, Heidi L.
    Wrobleski, Stephen T.
    Sherwood, Trevor C.
    [J]. REACTION CHEMISTRY & ENGINEERING, 2022, 7 (09) : 1945 - 1953
  • [6] Photocatalysis in the Life Science Industry
    Candish, Lisa
    Collins, Karl D.
    Cook, Gemma C.
    Douglas, James J.
    Gomez-Suarez, Adrian
    Jolit, Anais
    Keess, Sebastian
    [J]. CHEMICAL REVIEWS, 2022, 122 (02) : 2907 - 2980
  • [7] Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis
    Chan, Amy Y.
    Perry, Ian B.
    Bissonnette, Noah B.
    Buksh, Benito F.
    Edwards, Grant A.
    Frye, Lucas, I
    Garry, Olivia L.
    Lavagnino, Marissa N.
    Li, Beryl X.
    Liang, Yufan
    Mao, Edna
    Millet, Agustin
    Oakley, James, V
    Reed, Nicholas L.
    Sakai, Holt A.
    Seath, Ciaran P.
    MacMillan, David W. C.
    [J]. CHEMICAL REVIEWS, 2022, 122 (02) : 1485 - 1542
  • [8] 3-Amino-fluorene-2,4-dicarbonitriles (AFDCs) as Photocatalysts for the Decarboxylative Arylation of α-Amino Acids and α-Oxy Acids with Arylnitriles
    Chen, Yiyang
    Lu, Ping
    Wang, Yanguang
    [J]. ORGANIC LETTERS, 2019, 21 (07) : 2130 - 2133
  • [9] Bifunctional sulfilimines enable synthesis of multiple N-heterocycles from alkenes
    Cheng, Qiang
    Bai, Zibo
    Tewari, Srija
    Ritter, Tobias
    [J]. NATURE CHEMISTRY, 2022, 14 (08) : 898 - +
  • [10] Dyckman A. J., 2022, 4-Azaindole Compounds, Patent No. [US20220340555, 20220340555]