Synthesis of phenolic derivatives via photoredox formal [4 + 2] tandem annulation of α-bromoketones and terminal alkynes
Ma, Yingchun; Yu, Ping; Shang, Guobao; Hu, Jingqi; Zhang, Zilong; Shi, Lou; Chang, Qiaowen; Sun, Shaoguang; Liang, Deqiang; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D5OB01596K

data_7160857
_publ_section_title
;
 Synthesis of phenolic derivatives via photoredox formal [4 + 2] tandem
 annulation of \a-bromoketones and terminal alkynes
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D5OB01596K
_journal_year                    2025
_chemical_formula_moiety         '2(C24 H18 O2)'
_chemical_formula_sum            'C48 H36 O4'
_chemical_formula_weight         676.77
_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
_audit_creation_date             2024-11-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2025-04-30 deposited with the CCDC.	2025-11-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.9720(10)
_cell_angle_beta                 103.3140(10)
_cell_angle_gamma                96.0790(10)
_cell_formula_units_Z            2
_cell_length_a                   9.6426(3)
_cell_length_b                   12.3442(3)
_cell_length_c                   15.2224(4)
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      67.568
_cell_measurement_theta_min      2.335
_cell_volume                     1751.71(8)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26293
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.278
_diffrn_reflns_theta_min         2.986
_exptl_absorpt_coefficient_mu    0.634
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.127
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.248
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         6410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.248
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0542
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1609
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5581
_reflns_number_total             6410
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01596k2.cif
_cod_data_source_block           kmxy2024_0m
_cod_database_code               7160857
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.873
_shelx_estimated_absorpt_t_min   0.777
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00W(H00A,H00B), C013(H01C,H01H)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00D), C00C(H00C), C00D(H00E), C00F(H00F), C00K(H00K), C00L(H00L),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U),
 C00V(H00V), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011),
 C012(H012), C014(H014), C015(H015), C016(H016), C017(H017), C018(H018),
 C019(H019), C01A(H01A), C01B(H01B), C01C(H01I), C01D(H01D), C01E(H01E),
 C01F(H01F), C01G(H01G)
;
_shelx_res_checksum              22677
_olex2_submission_special_instructions 'No special instructions were received'