Chemoselective synthesis of multi-functionalized alkynes and alkenes <i>via</i> transition-metal-free iodination of terminal alkynes.
Lee, Anjun; Suresh, Sundaram; Du, Bo-Xun; Han, Xinlun; Yao, Ching-Fa; Organic & biomolecular chemistry 24 (2026) 1016–1020; doi:10.1039/d5ob01753j

data_7160931
_publ_section_title
;
 Chemoselective synthesis of multi-functionalized alkynes and alkenes
 <i>via</i> transition-metal-free iodination of terminal alkynes.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1016
_journal_page_last               1020
_journal_paper_doi               10.1039/d5ob01753j
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C10 H9 I3 O2'
_chemical_formula_sum            'C10 H9 I3 O2'
_chemical_formula_weight         541.87
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2025-10-31 deposited with the CCDC.	2026-01-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.695(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6310(9)
_cell_length_b                   5.3074(4)
_cell_length_c                   13.5696(11)
_cell_measurement_reflns_used    7467
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.19
_cell_measurement_theta_min      2.50
_cell_volume                     691.29(10)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10770
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.286
_diffrn_reflns_theta_min         2.499
_exptl_absorpt_coefficient_mu    6.763
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.603
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 1052 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2467
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.914
_refine_ls_R_factor_all          0.0193
_refine_ls_R_factor_gt           0.0187
_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^)+(0.0387P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0519
_refine_ls_wR_factor_ref         0.0526
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                2420
_reflns_number_total             2467
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01753j2.cif
_cod_data_source_block           shelx_CCDC3
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7160931
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.102
_shelx_estimated_absorpt_t_max   0.935
_shelx_res_checksum              84148