Facile synthesis of multisubstituted 2,3-dihydrofurans <i>via</i> intermolecular cyclization of enals or alkyl/aryl aldehydes with acyl-stabilized sulfur ylides.
Su, Yin; Sun, Ziyi; Zhao, Quansheng; Fu, Liang; Chemical communications (Cambridge, England) 62 (2026) 2585–2588; doi:10.1039/d5cc06219e

data_7135486
_publ_section_title
;
 Facile synthesis of multisubstituted 2,3-dihydrofurans <i>via</i>
 intermolecular cyclization of enals or alkyl/aryl aldehydes with
 acyl-stabilized sulfur ylides.
;
_journal_issue                   8
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2585
_journal_page_last               2588
_journal_paper_doi               10.1039/d5cc06219e
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C24 H17 Br O2 S'
_chemical_formula_sum            'C24 H17 Br O2 S'
_chemical_formula_weight         449.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-03-27
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-02-27 deposited with the CCDC.	2025-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                89.547(8)
_cell_angle_beta                 78.444(7)
_cell_angle_gamma                73.771(7)
_cell_formula_units_Z            4
_cell_length_a                   9.778(3)
_cell_length_b                   14.662(5)
_cell_length_c                   15.350(5)
_cell_measurement_reflns_used    9006
_cell_measurement_temperature    296.15(10)
_cell_measurement_theta_max      22.948
_cell_measurement_theta_min      2.712
_cell_volume                     2067.4(12)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker D8 Venture diffractometer'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15(10)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0920
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            64006
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         2.712
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.106
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0861 before and 0.0555 after correction.
The Ratio of minimum to maximum transmission is 0.8392.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     590
_refine_ls_number_reflns         7273
_refine_ls_number_restraints     301
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+2.0409P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1404
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3932
_reflns_number_total             7273
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06219e2.cif
_cod_data_source_block           20240327b
_cod_original_cell_volume        2067.5(11)
_cod_database_code               7135486
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.654
_shelx_estimated_absorpt_t_min   0.621
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C5-C7A \\sim C5-C11A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C36 \\sim C39 \\sim C37 \\sim C38 \\sim C40 \\sim C41 \\sim C37A \\sim C38A
\\sim C40A \\sim C41A: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim C7A \\sim C8A \\sim C9A
\\sim C10A \\sim C11A: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Same fragment restrains
{C6, C7A, C8A, C9A, C10A, C11A} sigma for 1-2: 0.01, 1-3: 0.04
as in
{C6, C7, C8, C9, C10, C11}
{C36, C39, C37A, C38A, C40A, C41A} sigma for 1-2: 0.01, 1-3: 0.04
as in
{C36, C39, C37, C38, C40, C41}
5. Others
 Sof(C37A)=Sof(H37A)=Sof(C38A)=Sof(H38A)=Sof(C40A)=Sof(H40A)=Sof(C41A)=
 Sof(H41A)=1-FVAR(1)
 Sof(C37)=Sof(H37)=Sof(C38)=Sof(H38)=Sof(C40)=Sof(H40)=Sof(C41)=Sof(H41)=FVAR(1)
 Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=
 Sof(C11A)=Sof(H11A)=1-FVAR(2)
 Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=Sof(C11)=
 Sof(H11)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16),
 C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C7A(H7A), C8A(H8A),
  C9A(H9A), C10A(H10A), C11A(H11A), C31(H31), C32(H32), C33(H33), C34(H34),
 C35(H35), C37(H37), C38(H38), C40(H40), C41(H41), C44(H44), C45(H45), C46(H46),
  C47(H47), C48(H48), C37A(H37A), C38A(H38A), C40A(H40A), C41A(H41A)
6.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C42(H42A,H42B,H42C)
;
_shelx_res_checksum              25957
_shelx_hkl_checksum              83047
_olex2_submission_special_instructions 'No special instructions were received'