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_7160928
_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         'C9 H7 N O3'
_chemical_formula_sum            'C9 H7 N O3'
_chemical_formula_weight         177.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2025-12-02 deposited with the CCDC.	2026-01-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.279(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4487(3)
_cell_length_b                   13.7929(6)
_cell_length_c                   7.9813(3)
_cell_measurement_reflns_used    5099
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      66.78
_cell_measurement_theta_min      6.42
_cell_volume                     817.71(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5160
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        66.770
_diffrn_reflns_theta_max         66.770
_diffrn_reflns_theta_min         6.418
_exptl_absorpt_coefficient_mu    0.929
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.606
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.540
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1417
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0674
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1347P)^2^+0.3130P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1902
_refine_ls_wR_factor_ref         0.2004
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1242
_reflns_number_total             1417
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01753j2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7160928
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.606
_shelx_estimated_absorpt_t_max   0.964
_shelx_res_checksum              93542